tagTranssexuals & CrossdressersJay's Sex Club Adventures Ch. 21

Jay's Sex Club Adventures Ch. 21

byWhiskeyIsGood©

Well, back by popular demand. It's time to continue Jay's Sex Club Adventures. I've been getting a lot of requests from people, asking me if I intend to continue this series. It's been a few years and at first, I really wasn't interested but after a while, I decided it was worth a try. I have a lot in store for our favorite characters. I hope you all enjoy. If you are new to this series, I strongly suggest reading it from the beginning, so you can understand (and also my recent upload, How Rob Met Annie...it's a spin-off but it is important to the main series)

Whiskey


*****

The sound of my alarm clock blasting in my ear, woke me from a deep state of sleep, that I missed the moment I opened my eyes. With a groan, I reached over to the nightstand and grabbed my cell phone, pressing the "off" button on the alarm.

I set the phone back down and contemplated for a moment, trying to fall back to sleep...I couldn't afford to sleep any longer though. It was already seven thirty in the morning and I had to be in work, by nine o'clock. Holly lay beside me, with my back towards her, her right arm wrapped around my waist and in the spooning position, I could feel her cock poking at my backside.

I heard her moan lightly behind me, pressing closer to me and moving her hand up under my shirt and over my smooth chest.

"Morning," she muttered, sounding very groggy.

"Morning..."

I felt her warm lips pressing against the back of my neck, her cock pressing harder against my ass, through the fabric of my boxers. I groaned, my own cock standing at full attention now and I pushed back against her, as she started dry humping me.

"I have to get ready for work," I sighed.

I really didn't feel like going in...I would have much rather stayed in bed and let my girlfriend, have her way with me.

"No time for a quickie?"

"It's already seven thirty."

"Mmm, but I'm so horny..."

I turned over onto my back and Holly propped herself up on her elbow, pressing her lips against mine and sliding her tongue into my mouth. I moaned, kissing her back and wrapping my arms around her...we were both in the same state of mind.

I wanted to mess around just as much as she did...fuck it, I thought to myself.

I forced her to lay back and slid my hand down under the blankets, past the waist band of her panties and my fingers curled around her throbbing cock; she really was hard. I began stroking her cock, my hand slowly gliding up and down the length of her shaft and Holly moaned, as I started kissing her neck.

I moved down some and lifted her t-shirt up, revealing those beautiful breasts and perky nipples. I started sucking on her nipples, still stroking her throbbing cock at the same time.

Then I moved down even further, kissing my way over her belly and down to her waist.

"God, Jay...don't tease me!"

I slid underneath the blankets and came face to face, with my girlfriends big, throbbing cock. Holding it with one hand at the base, I began swirling my tongue around the head of her shaft. Holly moved her hands down under the covers, running them through my hair and she shivered, as I continued to tease her with my tongue.

I ran my tongue down the length of her shaft, then slowly back up to the tip again and back down the length once again. I continued doing this for a few very long seconds, before sliding all the way down to her balls and started tonguing them.

As my tongue lapped at her heavy balls, I pumped her cock with my left hand and used the other one to reach up and tease one of her nipples. Holly was starting to pant now, as I started sucking on her balls, working my way up to the main event.

"Damn it...Jay...just s-suck my...fucking cock!"

She was ready; I was ready too, I thought to myself. Hell, sometimes teasing her was teasing myself, as well. I wanted it just as badly as she did, so I dropped the foreplay and within seconds, her cock was in my mouth. I wrapped my lips around her and started sucking, bobbing my head up and down. Her hands moved over my head again and pushed it further down, until she slid right into my throat and I gagged.

I could feel her balls pressing against my chin, my eyes welling up a bit and I started practically drooling all over her dick.

In all the time that I had spent with Holly, I had gotten really good at sucking her cock. Sure, there were other girls who had helped her teach me the art of the blowjob; but I didn't like sucking anyone's cock, half as much as I loved sucking hers. Every sound that she made, seemed to turn me on even more...my own cock was so fucking hard, it was almost painful. I reached down between my legs and started stroking myself.

"Fuck...cumming...I'm gonna...cum..."

I quickened my pace, focusing on my deep throat skills. Holly started breathing heavier and took a fistful of my hair in her hand, panting and moaning and writhing around underneath of me.

"I'm gonna cum!"

I backed off just a little, until only her head was between my lips and I moaned, as she started to cum. She immediately flooded my mouth, with her warm and sticky fluids. The sweet flavor washed over my tongue and I kept sucking on the head of her cock and gently rubbing her balls, trying to milk her dry. She moaned and moaned even louder, riding her orgasm until it was complete and I had drained her balls of every drop of cum.

As she pumped her load into my mouth, my own cock gave a jerk and a twitch and I gasped. I started moaning and groaning against her cock, and I felt my cum running down my fingers. It amazed me sometimes, that giving her a blowjob sometimes turned me on so much, that I could cum just from that.

I swallowed it all and came up from under the covers, my cheeks flushed and my hair sticking to my head with sweat. Holly smiled at me, still breathing heavily and brushed the hair out of my face. "That was great."

"I agree," I replied, kissing her on the lips and laying back down beside her.

"You probably really should, get ready for work now...look at the clock!"

I glanced over at my nightstand and groaned; the clock read eight o'clock. I had one hour to get in the shower, get dressed, make some coffee and get my ass to work.

"Do I have to go in today?"

"I really wish you didn't," Holly said, resting her head on my chest. "I'd rather you stay home and suck my cock all day."

"If only that were possible, I would be one happy guy."

"And I'd be one happy girl," she laughed.

I finally forced myself out of bed, stretching and making my way towards the bathroom. Holly got up and made her way downstairs to the kitchen, prepping a pot of coffee for me, so I wouldn't have to worry about doing it myself. I took a moment to relieve my bladder, before stepping into the shower and washing my body.

After I dried off, I brushed my teeth and swished some mouthwash around for a moment, before quickly heading downstairs to meet Holly, in the kitchen.

"I have to get going," I said, as she handed me a cup of coffee.

I gave her a quick kiss and she hugged me tightly.

"What are we doing when you get home, tonight?"

"Not sure...it's Friday, so we'll do something."

"Call me on your break and we'll talk about it, okay?"

"You got it babe."

One more kiss and I was out the door, jumping in my car and speeding out of the driveway. I got to work with ten minutes to spare and sighed, relieved to know that I wouldn't be late that day. I'd been late at least three times, in the last couple of weeks...I really didn't need anymore warnings from management. I clocked in right on time and got started right away.

The day went by fast and during my break, I called Holly, like I promised her I would. We talked about what we wanted to do that night and eventually decided, to invite Rob and Annie over to hang out for a while. They had just gotten back from their honeymoon and we were both looking forward, to talking about things had gone for the two newly weds.

Rob and Annie got married about two weeks ago. It was a beautiful wedding and I was proud of my friend, and felt honored to have been his best man. Of course, Rob said he wouldn't have asked anyone other than me, to fill that role. We had been best friends all our lives and it was a mutual agreement, that we would be the best man at each others weddings. That's something I needed to talk to him about, actually...

I had spoken with Rob briefly at his own wedding, about something that could very likely be happening soon; I wanted to propose to Holly. I wanted to make her my wife and spend the rest of my life, with her at my side. The ring had already been purchased and I had spent quite a bit of money on it, but it was well worth the cash I had spent.

With that out of the way, there was only one thing to establish; the right time and place to ask the question. I wanted it to be perfect and I knew, it would never be one hundred percent perfect; but it had to be good enough. I was hoping Rob could help me plan all of this stuff and maybe even put my nerves at rest, so I could stop obsessing.

I sent him a text, after I hung up with Holly and asked if he and Annie were free that night.

Rob: We're not doing anything tonight, buddy. What's up?

I asked if they wanted to come over and have a few beers, to which he replied rather quickly, "Sure thing. Be there around 8:00?"

"Sounds good," I wrote back. "See you guys tonight."

I finished up my shift and by 5:00, I was on my way back home. I stopped at the liquor store on the way back and grabbed a bottle of whiskey for me and Rob to split, as well as a bottle of whine for Holly. When I got home, I decided to cook some burgers on the grill for everyone to eat.

Rob and Annie arrived at 8:00 sharp, just like he said and immediately, Holly and I were bombarding them with questions about how their honeymoon had gone. We talked about that for a while and once we finished eating, we sat down at the table in the yard and started drinking. I was waiting for the right moment to bring up my plans to Rob; obviously, I had to wait until Holly wasn't around.

Luckily, Holly and Annie decided to go inside and use the bathroom, leaving Rob and I alone, so I could finally bring up what was on my mind to him.

"You alright buddy? You look nervous," Rob said, starting the conversation for me.

"Yeah, I'm good dude; I need to talk to you though."

"Sure, what's up?"

"Remember what we talked about, at your reception?"

He thought about it for a moment and then a grin crept across his face, as he nodded his head in understanding.

"Let me show you something," I said.

I stood up and reached into my pocket, pulling out a small, square shaped box. I sat back down and leaned across the table, opening the box and revealing a very large diamond engagement ring. "Holy fuck, dude!"

Rob's eyes went wide, practically popping out of their sockets.

"How much fucking money, did you spend on that?"

"More than you can imagine," I replied, with a laugh.

"Holly is going to love that thing, Jay. You really out did yourself on this one...when are you gonna ask her?"

"That's what I wanted to talk to you about," I said, shutting the box and shoving it back into my pocket again.

"I have no idea when the hell, I want to do this. It's got to be fucking perfect man; she has to have absolutely no idea that it's coming."

"So you're trying to plan the perfect proposal, huh? Good luck with that. I was the same way, when I asked Annie."

"And was it perfect?"

"I don't think so," he laughed.

"But Annie sure was happy. I feel I could have done a whole lot better, but...at least she was satisfied. I took her to the beach and waited until the sun was setting. Nice cool breeze, the water washing up under our feet...man, she was so caught up in nature, she had no idea what I was about to do. Then I dropped on one knee and pulled out the ring...she looked like a kid in a candy shop."

I couldn't help but laugh, as Rob explained to me his story of when he proposed to Annie. I could see in his eyes, he was still living the memory like it was yesterday. That's how it had to be with Holly. She had to be able to look back at it, ten years from now and feel like it was only a day ago, that I had asked her to marry me.

"How about you do it next month, when we go down Wildwood? Holly loves the beach, right? They do fireworks every Friday night down there, you could drop the question on the beach, under the boardwalk, with fireworks going off...I bet she would love something like that, Jay!"

"That just might work..."

We were planning a group trip down the shore next month. It had been the works for a while now. We were all pitching in together and renting a house down there, with two bedrooms, one floor, a nice yard with a fire pit and a swimming pool...and it was only right down the street, from the boardwalk and the beach.

"I think that's when I'm going to do it...you think she'll say yes?"

"Jay, that's a stupid question bro...why the fuck wouldn't she?"

"I don't know," I sighed. "I guess, I'm just...nervous?"

"Nothing to be nervous about," Rob reassured me.

"Holly loves you so fucking much; there's no way in hell, she would say anything other than yes. I'm telling you Jay, this is going to work out just fine; I promise!"

"Thanks dude..."

I believed him. Rob was right, there was no reason why Holly would say no, if I asked her to marry me. We had talked about marriage in the past and she had always been very open to the idea. We'd been together long enough and we had been through more than enough, as a couple. I was positive that the two of us would make a great husband and wife, and we would spend the rest of our lives together.

My conversation with Rob ended just as Holly and Annie came back outside, sitting back at the table with us. They were both pretty drunk by now and laughing it up, like a couple of school girls.

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

"Oh nothing," Annie replied. "I was just telling Holly about our first night together...as husband and wife. And how good you fucked my ass."

"Getting a bit personal there, huh?"

We all got a good laugh, as Annie carried on telling Holly about all the hot sex, she and Rob had during their honeymoon. Apparently that first night, Annie was the one taking it in the ass...happily of course...but during the actual honeymoon, the roles had shifted and Rob spent pretty much their entire time away, bent over and getting pounded by his new wife. By the end of it all, I couldn't help but crack a joke. "Your ass must be pretty sore by now, after all that fucking, huh buddy?"

"I'll live," he shrugged. "I guess it's pay back, for all the times I made her walk funny...right babe?"

"Mmm, that's a good way to look at it."

"Better watch it Jay," Holly chimed in.

"That blowjob this morning was real hot...but tonight, I'm going to fuck your ass so hard, you and Rob will have a few things in common by the time I'm done with you."

"Is that a threat?"

Holly grinned, leaning across the table and giving me a kiss on the lips.

"I don't make threats honey; I make promises."

We all laughed and Rob poked fun at me for a moment, taking a sip of his whiskey and the conversation carried on. We sat outback and kept talking for a few more hours, until well after midnight. None of us had work the next day, since it was Saturday, so we were able to kick back and have fun as long as we wanted.

Rob and Annie didn't leave until almost two o'clock in the morning, and when they did, I could hardly wait to get upstairs to our room and see what Holly had in store for me.

Holly had gone inside ahead of me, while I walked Rob and Annie to their car and made them promise to text when they got home. When they pulled out of the driveway, I rushed back into the house and locked all the doors for the night. Then up the stairs I ran, straight into the room and found Holly in bed...completely nude and already very hard.

Her cock was standing straight up and she was slowly stroking it, smiling at me, as her hand glided up and down her shaft.

"Took you long enough."

"Sorry to keep you waiting," I said, sheepishly.

"Don't apologize; just get your ass over here!"

I quickly pulled my shirt over my head, tossing it to the floor and slipping out of my shorts. Removing my boxers, I climbed into the bed and Holly wrapped her arms around me, pulling me close and we started kissing. Our tongues dancing, our hands began to roam and soon enough, I was lying on my back and Holly was busy tea bagging me. Her cock and balls hung right over my face and I opened my mouth, eagerly waiting, as she lowered herself down until her balls were right within tongues reach.

I licked and sucked on the for a few moments, before she shoved her cock down my throat and started mouth fucking me. I gagged and choked, slurping and spitting, my own cock oozing pre-cum. Holly turned me over onto my stomach and after applying some lube, she slipped her fingers into my ass and started gently massaging my prostate.

I moaned, as her fingers slid in and out of my hole.

My cock swelled up and started oozing even more, my balls aching for release already. I reached down to touch myself but Holly swatted my hand, pushing it away and pulling her cock from my mouth. She turned around and shoved her ass in my face, wrapping her lips around my cock and started sucking. I groaned, my mouth wide open and she slipped back between my lips again.

We were sucking each other off now; I loved 69.

As Holly sucked my cock, she continued working my ass with her fingers for a few minutes...it didn't last too long, though.

Her cock was throbbing and we both knew, what she really wanted. Once again, I turned over onto my stomach and after smacking my ass quite hard, Holly grabbed the bottle of lube and poured the cold lubricant all over my ass crack. I gasped, surprised at how cold it was and Holly proceeded to add some to her cock as well, stroking it until it was nice and slick. She wasted no time from that point, lining the head of her cock up with my hole and thrusting right into me.

I gave a low grunt and gripped the sheets, instinctively pushing back against her and she quickly bottomed out.

Her hands moved to my hips and Holly began pounding, driving her cock in and out of my ass, with no mercy. She hadn't been lying when she said all that stuff outside; she really was going at it and I was loving every second of it, too.

Since we had moved in together, in my Uncle's house, the sex that Holly and I had, had become much more intense. She seemed to really enjoy being the dominant one in the bedroom. She always liked it before of course but, she had become much more interested in my ass then she was before. I had grown to enjoy the role reversal quite a bit, myself...sometimes, I even enjoyed being a bottom even more than I did being a top.

That didn't mean that Holly no longer liked to bottom for me. She still loved my cock and I still loved giving it to her, whenever she wanted it.

We rolled over in the bed, a sweaty mess already and now I was on top of her, riding her cock and bouncing up and down in her lap. Her hands stayed at my hips and I watched as her tits jiggled, as she lifted her ass off of the mattress and fucked me.

I leaned back on both hands, my cock slapping hard against my stomach. Holly reached up and grabbed my dick, stroking it and licking her lips, as I continued riding her. "I want you to cum for me baby," she whispered, staring up at me with lust.

"Are you gonna cum for me, Jay?"

"Fuck yeah baby," I replied, panting and sweating furiously. "I'm almost...there...almost...ready..."

Resuming full control once again, Holly flipped me onto my back and lifted my legs high up into the air. She drove herself harder and harder, into my gaping ass and I threw my hands up in the air and moved them behind my head. Moaning louder now, my cock began to pulsate in her hand; I was almost there.

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byWhiskeyIsGood© 7 comments/ 12414 views/ 18 favorites

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