tagTranssexuals & CrossdressersJay's Sex Club Adventures Ch. 22

Jay's Sex Club Adventures Ch. 22

byWhiskeyIsGood©

This one didn't turn out to be as long, as I originally intended...sorry about that. But I definitely intend for the next chapter, to be a bit longer and full of some more action...and drama. But that's been a pretty consistent thing in this series lol. I hope you enjoy and look forward to the next chapter. As always, feedback is much appreciated.

Whiskey


*****

"CONGRATULATIONS, JAY AND HOLLY!"

The huge banner hung over the bar area, with big, bold letters in the color of the rainbow that could be seen from a mile away. As Holly and I entered The Raven, everyone began to cheer and raised their glasses to salute us both. "Looks like someone already told them the good news," Holly giggled.

"I wonder who that could have been," I replied, sarcastically.

We both knew who it was; Rob and Annie.

Our two dear friends had been so excited, to learn that we were finally planning on getting married. Throughout the rest of our vacation time in Wildwood, it was all the two could talk about. You would have thought it was THEM getting married, all over again, with the way they were going on about it...it was cute though, in Holly's words. No doubt in my mind, it must have been Rob and Annie who arranged this obvious celebration.

We were instantly greeted by our closest friends; Jen, Rob, Annie and all of the girls that I had come to know at the club. They all greeted us with hugs and congratulated us, obviously very excited about the good news. Holly was whisked away by Jen and two other girls, Annie being one of them, to talk about wedding things. Rob and I made our way to the bar and ordered a couple of drinks.

"So," I said, with a sly grin.

"Yeah, it was me; sorry buddy, I couldn't keep my mouth shut."

"I figured as much," I laughed. "It's alright, but this party?"

"Hey, that wasn't our idea! Once we told everyone the good news, word got back to management and since everyone knows you both so well here...they decided to do something for you."

I smiled, surprised to hear that it had all been the club managers idea. Lizzy was the clubs owner; I had only met her on a few occasions, but she always seemed pretty nice. Like all of the girls at The Raven, Lizzy was a transsexual and apparently loved to party, just as much as her customers. She didn't get to hang out at the place that often though...being the owner kept her busy enough, that she didn't have a whole lot of time.

"Holly and I, will have to thank her at some point."

Rob looked up from his beer and pointed across the dance floor, towards a row of tables and chairs. "Looks like you'll get your chance tonight," he said. "I didn't realize she was here!"

Sure enough, across the room stood a very tall blonde. She had piercing blue eyes, perfect tits and looked absolutely gorgeous, as always; that was Lizzy.

I jumped, as someone's hand made contact with my shoulder and I turned around, to find Holly smiling at me.

"This is great, isn't it? Who'd have thought, they would do something like this for the two of us?"

"Apparently, it was Lizzy's idea," I said, pointing towards the club owner.

"No way! Seriously? Jay, let's go thank her."

Holly took my hand, pulling me from my chair at the bar and leading me across the dance floor, beer in hand. Lizzy looked up from the two girls that she had been talking with and smiled at us, immediately looking bright and cheerful, as we approached.

"You did NOT have to do this," Holly shouted, throwing her arms around Lizzy and hugging her tight.

"Are you kidding me, of course I did! You guys are two of my biggest club members; you're very popular here and we're all very happy, to see that you're getting married."

"It's very appreciated," I said, with a smile.

"We didn't expect everyone here, to already know about it though...apparently, Rob and Annie couldn't wait for us to tell everyone the good news."

"Yeah, those two really love you guys, you know that?"

We all laughed; I knew Rob and Annie definitely cared, a great deal about the both of us.

We chatted with Lizzy for a few minutes longer, before heading back towards the bar and grabbing a few more drinks. By this point, the club was packed and the music was blasting through the speakers. It was a Friday night, so of course we weren't the highlight of the night but, we definitely were mentioned by the DJ a few times. When we were mentioned, everyone happily cheered and congratulated us, over and over again.

The night was moving quickly and me, Holly, Rob and Annie had all taken up a table in a corner of the bar. Pressing 11:30 at night, we were all starting to feel the effects of the alcohol. I took a shot of Jameson with Rob and as I set the shot glass down, and looked up from the table, my eyes met with someone I had not seen in a few months; Kendra.

She noticed us just as quickly as I had noticed her, cracking a big grin and started across the room in our direction.

"Hey you two," she said, in her usual husky voice.

"Kendra! Long time no see," Holly said, standing up and giving the tall dark Mistress a hug.

"Congratulations to you both; I just heard the good news. Jay's gonna be a married man soon, huh? How do you feel about that baby boy?"

I blushed and smiled. "I'm excited," I replied, wrapping my arms around Holly and kissing her on the cheek.

"You two really are in love, aren't you?"

"More than that," Holly replied with a smile. "We're best friends."

"Let me buy you both a drink!"

Before either of us could protest, Kendra had signaled one of the waitresses over and ordered shots for all of us; Rob and Annie included, of course. We threw back our drinks and Kendra sat down at the table with us, nursing the beer she had brought over with her.

"So, do you two have any plans for the wedding yet?" Kendra asked, curiously.

"Not yet," I replied. "We're just in the process of breaking the news to everyone. We haven't had the chance to start planning."

"Well, I know I can't wait to watch you two tie the knot. And Holly, you are one lucky girl, to be able to say that sweet white ass is gonna belong to you, for the rest of your lives."

"Oh, it already belonged to me," Holly said.

Holly, Annie and Kendra all started laughing and I chuckled, blushing as I threw back another shot.

"You know," Kendra continued.

"I apologize, if this is too much to ask...but it would be great, if I could have some fun with Jay one more time...before you two make it official."

I was a bit surprised that she had asked such a question, but then again, it wasn't too out of the ordinary for Kendra. I knew all to well, how attached she was to me and my...booty, as she liked to call it. What really took me by surprise though, was Holly's response.

"Sure!"

I looked at my fiance with shock, but smiled at her and she smiled drunkenly right back at me.

"I mean, if Jay wants to anyway! What do you think baby? You want some of Kendra's big cock, one last time?"

"Holly...are you sure it's-"

"It's totally fine," she whispered, biting her lower lip.

"Only one condition though..."

"The bride sets the rules," Kendra grinned.

"I get to watch...if you're both okay with me watching, then I'm okay with you doing the nasty together...one last time."

I chuckled and shrugged my shoulders. "It's alright with me...but are you SURE you're okay with me doing it?"

"It's okay, really; the thought of Kendra pounding that sexy ass of yours, has always gotten me hard, to be honest."

Another surprise; apparently my fiance liked to fantasize about me, getting fucked by Kendra.

"Well, it's a deal then," I said.

"Mmm, I can't wait to get a piece of that booty again," Kendra laughed.

Holly stood up, legs wobbling just a little and chugging the rest of her beer.

"Who said anything, about having to wait?"

"To the basement?" Kendra asked, with a grin.

"And beyond!" Holly shouted, causing everyone to laugh.

Rob leaned over the table and gave me a pat on the shoulder. "Have fun buddy...and remember how sore you were, last time you took that cock."

"Don't remind me," I laughed, rolling my eyes.

Kendra took my hand, pulling me out of my booth and Holly stood up behind me. She took my other hand and both girls proceeded to lead me, towards the staircase that led down into the basement.

We reached the bottom of the steps and Kendra immediately pulled me, towards the first vacant room she could find. She opened the door and the three of us stepped inside, the door slamming shut behind us, and Holly quickly locked it.

Without a word, Kendra shoved me onto the mattress in the corner of the dim lit room. The walls were painted to look like a very beautiful beach resort and the room smelled like cherries. Holly took a seat in a chair, on the other end of the room and watched, as Kendra climbed onto the bed with me.

"It's been so long, baby boy..."

"Yeah...it has, hasn't it," I said, nervously.

"Good sex is hard to come by, Jay; but every time I get to fuck your sweet little ass, it's like a dream come true for me."

"Ha...it's always fun for me too."

Kendra leaned in and kissed me on the lips, tongue sliding into my mouth and her hands began to roam. She slid them both up the front of my shirt and started teasing my nipples, gently pinching and rubbing them. Then her other hand, slid down and started working at my belt. Within seconds, my pants were undone and she had yanked them from my body, tossing them to the floor. My cock was standing at full attention, as Kendra stood up and started to strip from her own clothing.

She hooked her thumbs under the elastic band of her panties, slowly moving them down the length of her long, dark legs and stepping out of them. There it was; that huge, black cock, that I had truthfully kind of missed. It's the feeling you get, when you didn't realize how much you missed something, until you actually see it again.

Holly was still sitting in her corner of the room, but had removed her own clothes now and was already stroking her rock hard cock, as she watched the scene unfold before her. Kendra climbed back onto the mattress again, her lips returning to mine and my hand moved up her left thigh and towards her cock.

My fingers curled around her enormous shaft, and I began to slowly stroke her cock for her. She pulled my head towards her breasts and I began licking, and sucking on her nipples.

"Mm, that's it baby boy; suck on them titties."

I did just as she instructed but not for long, before she pulled away and sat her ass right down on my chest. That huge cock was right in front of me and before I could do anything, she slid forward and shoved it right between my lips.

I gagged, choking and slurping, as she wasted no time. Kendra was throat fucking me, moaning and panting and playing with her tits, as she slid her cock in and out of my mouth. She shoved all the way into my throat and held her position, her balls pressing against my chin, my eyes welling up with tears. My gag reflex had settled and I was able to take more of her cock...it had been so long, since I had sucked a dick as big as Kendra's. It took me a bit to adjust, but I did manage.

She pulled back for a moment, stroking herself and slapping her cock against my cheeks. I turned my head and looked towards my fiance...Holly was happily stroking her own cock and enjoying the show. I had worried for a bit, that she might just be pretending she was okay with all of this. Judging by how hard her own cock was though, I was pretty sure, I had been wrong. Clearly, Holly was very okay with the idea of this.

As much as Kendra seemed to be enjoying the oral attention, she seemed to have decided, that enough was enough. She quickly drew her cock back from between my lips, then proceeded to flip me over onto my stomach. Her whole body pressed down against mine and pushed me down into the mattress, as she began humping me. I could feel her cock, sliding back and forth along my ass crack, probing and teasing my hole, her tits pressing into my back. She reached for a bottle of lube, sitting on the table next to the bed and popped the cap open. I felt the cold, wet lubrication, pouring all over my asshole and she began rubbing it all up and down my crack.

She applied an extra amount to her cock, stroking it until she was nice and slick.

"You watching this, Holly baby?"

"Mmm, fuck yeah; fuck his ass for me, Kendra."

Wow, she was really enjoying this...who would have thought?

I relaxed my body, burying my face in the pillow and wiggled my ass for Kendra. She and Holly both laughed, as Kendra gave it a nice smack, the sound echoing through the room. She smacked me again and again, harder and harder each time. I was pretty sure by the time that she stopped, there had to be some bruising...of course I didn't mind, though. I loved being spanked.

Then the tip of her cock pressed up against my hole and unable to wait any longer, I pushed my ass back against her and she slipped straight in with ease.

"Fuuuck!" I yelled out, as Kendra immediately bottomed out.

"Ohhh, baby...I forgot how good that ass feels!"

Pushing me forward, Kendra kept one hand on the small of my back and the other on my left hip, as she began slowly gyrating her hips. In and out she moved, and I could feel every inch of that big black cock, sliding in and out of my tight hole.

I continued pushing back against her, meeting each of her thrusts and digging my nails into the sheets underneath of me. Soon, she was thrusting hard and fast, our bodies smacking together, the suction sound echoing all around us. I looked over at Holly again and my beautiful fiance was now stroking her cock furiously and moaning, as she enjoyed our performance.

"Hey honey," Kendra called out, to Holly.

"Why don't you come over here and help me out?"

With lust in her drunken eyes, Holly quickly stood up and moved towards the bed. Kendra turned me around, so that I was facing my fiance now and Holly grabbed a handful of my hair and roughly shoved her cock in my mouth. I gagged, as she slid right into my throat and began fucking my face. Kendra continued pounding my ass at the same time, slamming in and out, without any mercy.

Tag teamed by my sexy, ebony Mistress and my gorgeous fiance; I couldn't have asked for a hotter scenario.

This dynamic duo had me so turned on...my cock was leaking cum all over the bed! I couldn't help it, I was throbbing and pulsating, on the verge of an orgasm already. Without any warning, I started moaning and panting, my body trembling violently and my cock erupted and painted the sheets with cum. The two girls didn't stop though, Kendra still pounding my ass and Holly forcing her cock as deep into my throat as possible. Just like Holly and Kendra, my orgasm did not seem to stop either...it kept crashing over me, in waves...tidal waves.

Then Holly pulled back, moaning and panting, jerking her cock furiously...and exploded all over my face. I just barely managed to close my eyes, preventing her thick warm cum, from blinding me. At that point, Kendra yanked me towards her and flipped me onto my back, lifting my legs up high. She shoved her cock right back into my ass, placing both hands on either side of my head and started really ramming my ass. I cried out in pleasure, my cock stiffening up again and erupting immediately.

"Look at you, you dirty little slut! You're cumming so hard!" Kendra yelled, amazed by my intense orgasm.

When it stopped though, I was suddenly overcome by a feeling of exhaustion. Kendra wasn't anywhere near cumming yet and my ass, was starting to get rather sore...still, I kept on going, not wanting to stop until all three of us had gotten our rocks off.

Holly remained on the mattress, sitting right next to my head and stroking her cock, in an attempt to get hard again. My eyes went wide, at what I saw next...

Holly moved into position, shoving her dick between my lips again, but then she leaned forward and started making out with Kendra; I had not expected that! Both sexy ladies were towering over me, fucking me from both ends and making out at the same time. They were moaning and groaning, and soon they seemed to be paying more attention to each other, than they were to me...that didn't bother me though. I felt Kendra's cock getting harder inside of me, as she made out with my fiance.

Then she pulled out and Holly removed her cock from my mouth, both of them moving away from me and embracing each other.

"Wow," I thought to myself.

This had really taken an unexpected turn...but it was actually really hot!

Kendra pushed Holly onto her back, kissing her all over her neck and sucking on her tits. She moved between Holly's legs, forcing them apart and pressing her enormous cock against my fiance's asshole. I watched Holly's eyes go wide, as Kendra pushed forward and the head of her cock popped into her ass.

"Ohhh! Holy fuck!!"

Holly had the sexiest fucking look on her face, that I had ever seen. Kendra pushed her cock deeper and deeper into her asshole, spreading her wide open, until she bottomed out. She was buried all the way up to her balls, in Holly's tight ass and Holly wrapped her arms around Kendra and clung to her.

"F-Fuck...Jay!"

I kissed her on the lips, sliding my hand between her and Kendra, taking hold of her cock.

As Kendra began thrusting in and out, I started slowly stroking Holly's throbbing member.

As my hand pumped up and down the length of her shaft, Kendra started fucking her faster. Holly was breathing heavier now and her eyes were wide, with what appeared to be a mix of pain and pleasure...she didn't seem interested in stopping though. I took my hand away from her cock and that's when Kendra really let rip. Pushing Holly's legs as high up as they could go, Kendra began pounding away at the sexy black haired girl.

Holly gasped, crying out in pleasure and squeezing her eyes shut. The bed shook and I watched in awe, as Kendra hammered away at Holly's ass, like no tomorrow.

She stopped, pulled out and flipped Holly onto her stomach. Holly pushed herself up, onto her hands and knees and that's all she had time to do, before Kendra rammed her cock back into her ass. She grabbed Holly by the hips and resumed fucking her.

In this position, I could see Holly's cock, semi-erect and oozing pre-cum all over the place, flopping back and forth between her legs. I got behind the two girls and slid my head underneath of them, until Holly's cock was right over my face. I stretched my neck up a little and opened my mouth, closing my lips around her cock and Holly gasped.

She was fully erect within seconds and I started sucking and slurping, rubbing her balls, as Kendra continued pounding her ass. The combination of Kendra's dick, deep in her ass and my mouth wrapped around her own cock, was too much for Holly to handle. It only took a few more seconds, before my fiance was practically screaming in pleasure.

I felt her cock twitch and pulsate in my mouth, pouring a massive load of cum right down my throat. Kendra buried herself in Holly's ass and with a low grunt, she too let loose and started pumping the girl full of cum. I swallowed every drop of Holly's fluids, savoring the taste, before releasing her from my mouth and sliding out from underneath of her.

I pushed myself up onto my hands and knees, watching as Kendra slowly and carefully, withdrew herself from Holly's ass. Her cum immediately started oozing from Holly's gaping hole, running down her balls and dripping onto the bed. Holly slumped forward and buried her face in the pillow, gasping for air and glistening with sweat.

"That was unexpected, right Jay?" Kendra asked.

"Very..."

I was still really shocked at what had happened. One minute, it was me, on my hands and knees and getting rammed by Kendra. The next thing I knew, Kendra had turned her attention towards Holly and wound up fucking her too...it had been one of the hottest things, that I had ever experienced in my life.

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byWhiskeyIsGood© 8 comments/ 11562 views/ 24 favorites

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