Jay's Sex Club Adventures Ch. 24

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The Bachelor Party.
6.6k words
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Part 24 of the 25 part series

Updated 06/08/2023
Created 12/08/2013
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I pulled up at the airport, by the gate that my cousin would be coming through and parked the car. Leaning back in my seat, I turned off the engine and waited. Ryan's flight had landed about fifteen minutes earlier but, I knew it would take a bit for him to get his luggage and all that good stuff. I smiled to myself; it had been a long time since I last saw my cousin.

The idea of having so many people in my family at this wedding, people that I hadn't seen in years, it was a pleasant thought. I looked up and saw Ryan coming outside, carrying his suitcase and a bag slung over his shoulder. I jumped out of the car and made my way towards him, attempting to meet halfway.

"What's up cus?"

"Jay! Long time no fucking see!"

I embraced him in a hug and we gave each other a pat on the back, before I took the bag from him and walked him towards my car. "How was the flight?" I asked, trying to make conversation.

"You know how I am; I hate flying. It went alright though, I guess. Just left me feeling a bit sick to the stomach."

"Lot's of turbulence?"

"Not really...I just hate being in the sky."

We both laughed, as I opened the trunk and threw his luggage inside. I got back in the driver seat, as Ryan climbed into the passenger side and I turned the car back on.

"So I'm glad you could make it dude," I said. "Holly's looking forward to meeting you."

"It's a pleasure Jay. I'm looking forward to meeting her too...I've heard a lot of good things about her."

"She's amazing," I smiled. "I really love her."

Ryan smiled, nodding his head and gave me a pat on the shoulder. "I'm glad you found someone you can spend the rest of your life with, like that. I'm looking forward to this wedding."

It wasn't long before we were back at the house and I was helping Ryan carry his belongings inside. He would be staying in the guest room, right down the hall from where Holly and I slept. It had been a long time since Ryan had seen this place...probably ten years or something.

Much like me, Ryan had known Uncle Stan quite well. Like I said before, Uncle Stan had always been the "favorite Uncle" to all the kids when we were younger; Ryan was no exception. When he saw the old house, Ryan couldn't help but tear up a little as he felt the overwhelming sensation of nostalgia.

He was also very impressed at all the renovations that I had done, and how I had really fixed the place up nice and good. As we came back downstairs from the guest room, we ran into Holly, as she was coming out of the kitchen.

"You must be Holly?" Ryan asked, excitedly.

"And I'm guessing you're Ryan, correct?"

"That's me!"

We all laughed, as Ryan and Holly exchanged a brief hug and got to talking.

Ryan repeated his earlier remark, about having heard a lot of great things about Holly and how happy he was for the both of us. It was good to see the two of them get along so well, after only just meeting for the very first time.

"I'm going to have to make a run to the store," Holly said, giving me a kiss on the cheek.

"Do you want anything?"

"Maybe pick up a case of beer, if you can?"

"Sounds good to me," she agreed, before heading out the door.

I looked over at Ryan and smiled. "So, how about we go chill in the yard for a little while, until Holly gets back?"

"Sure," said Ryan.

We stepped out onto the back deck and sat down, both of us lighting up a cigarette and started talking, catching up on missed time. I told Ryan a lot about what we had in store for the wedding and the reception that we would be having afterwards. We got to talking about the bachelor party...Rob was in charge of that department. I didn't really know a whole lot, about what my friend had in store but, I told Ryan what little I did know. He seemed pretty excited.

"So, how's life out in Florida?" I asked, curiously.

"It's not too bad," he answered honestly. "A bit lonely..."

I understood...

Ryan's parents had passed away about a year or two ago, having been killed in a pretty bad car accident. He'd been on his own ever since but, from what I heard, he wasn't doing too bad for himself. I could imagine how lonely it probably was though.

"Don't you got a girlfriend or anything?"

To my surprise, that earned a bit of a laugh from Ryan.

"I'm not doing too well in the dating department," he admitted. "I've been single for well over a year now."

"No kidding...I mean, I always heard you were a-"

Ryan interjected, "A real ladies man?"

I chuckled, taking a drag of my cigarette and Ryan cocked his head to the left, staring out across the yard.

"I guess that's not exactly wrong," he continued.

"I've had my fair share of relationships."

"You make it sound like you're older then me," I laughed.

"Ha, yeah...well...I don't know. Sometimes I think I'm better off single, you know? Like something is just missing when it comes to dating."

I wasn't quite sure what he was trying to get at, but I listened to him, noticing the troubled look in his eyes. "Can I ask you a question?"

"Sure," I replied. "What's up?"

"I don't mean to sound like a dick or anything but..."

"Whatever it is, just spit it out."

Ryan hesitated for a moment, then looked back at me.

"There's rumor floating around the family...is it true...you know, about Holly?"

"Uh...what have you heard?"

"That...she's a transsexual?"

I was well past the point of keeping that secret from anyone but, I did know that not many people in the family were aware, aside from my parents. "It's true," I admitted.

"Again, I'm not trying to be an ass," Ryan continued.

"But I also heard...Uncle Stan was into that sort of thing too?"

"I don't know a whole lot about Uncle Stan," I replied. "I know that he was in a relationship, with a girl who was a transsexual. I'm not aware of too much of his dating history though."

Ryan fell silent after I finished that little bit, and I continued to wonder what exactly was playing on my cousin's mind right now. "Dude, you know you can talk to me...right?"

"I know, I know just...I'm getting there..."

I stood up, tossed my cigarette to the ground and stomped it out. I leaned against the railing that overlooked the yard, folding my arms over my chest and staring at Ryan with a serious look. "Come on dude; spit it out."

"I just...um...well...do you know other girls like that...besides Holly?"

Suddenly, I had an idea of where this was heading and I was pretty surprised but obviously not against it.

"Why would you ask?"

"I..."

"Ryan, are you interested in transsexual women?"

He looked up at me and chewing on his bottom lip, he nodded his head and I cracked a grin.

"Wow...I guess it does run in the family. We've got more in common then I thought."

"I guess so," Ryan laughed, his nerves seeming to settle a bit.

"I know quite a few girls, that you would be interested in."

"Would you be willing to set me up?"

"Have you ever been with a transsexual before?"

Ryan shook his head and I thought about it for a moment. It's not that I was against the idea, I just wasn't quite sure who the right girl would be for him, since he'd never experienced sex with a girl like that before. "I'll tell you what," I said, after a few moments.

"I'll talk to Rob and we'll see what we can do; I have a few friends, that I think would really like you."

"Thanks Jay...I really appreciate it."

"It's no problem," I smiled. "But why were you so nervous about telling me that, when you know I'm getting married to Holly? It's not like I'm going to hate you, or anything."

"I know...it's just I've never told anyone before."

"So I'm the first person, you've ever opened up to about that?"

Ryan laughed, nodding his head. "Pretty much."

"Wow," I chuckled. "I feel special."

Holly got back a few minutes later, and we helped her carry in the case of beer and a bag of ice. I washed out the cooler that we had in the yard and filled it up, setting it out on the back porch. We all sat outside and shared the 30 pack together, drinking, laughing and having a great time like always. Later that night, when Ryan went to bed, I decided to tell Holly about the information that my cousin had shared with me. We were laying in bed and watching TV when I brought it up to her.

"Guess what I learned about my cousin, today?"

"What's that?"

I smiled, sitting up next to her and shutting off the television for the night.

"Apparently, Uncle Stan and I aren't the only people in this family, who are attracted to transsexual women."

"What...no way! Are you serious?"

"Very," I laughed. "Ryan like's girls with something extra. He asked if I could set him up with someone; a date for the wedding."

"Oh wow," Holly laughed. "I wonder how many other people in your family, are into girls like me?"

"For all I know, there could be a lot more."

"So, who are you going to set him up with?"

I thought about it for a moment and cracked a grin.

"I was thinking maybe Kendra; she did tell me, she wanted me to help her find a steady boyfriend."

Holly looked at me like she wanted to laugh but, held it back as best she could manage.

"You want to set your cousin up, with the girl who has the biggest dick in the club? Has he ever even-"

"No, he's never done anything like that before."

"Jay, you of all people should know...Kendra isn't exactly the best person for a first timer. She'd split that kid in half!"

"I know, I'm kidding!"

Holly shook her head, but still smiled. "You're trying to kill your own cousin, aren't you?"

"He'd probably thank me later on," I continued, earning a playful smack from Holly.

"What? Yeah, she'd split him in half but it would only hurt for a few minutes...then you and I both know, how good it could feel."

Holly rolled her eyes and pushed herself up, rolling over on top of me and kissing me on the lips. "I'm about to split YOU in half in a minute!"

"Really? Sounds like fun."

I kissed her back, deeper this time and she slid her tongue into my mouth. She grabbed my arms and pinned them down above my head, holding them firmly in place and grinding against me. My cock instantly responded, growing to full attention and I could feel hers rising up as well. I pushed back against her and quickly managed, to overcome her and flip her onto her back. I was sitting on her lap now, still making out with her and dry humping her.

I could feel her throbbing cock, pressing against my ass through the fabric of my boxers; I wanted her so bad.

I slid down from her lap, pulling her pajama bottoms down and freeing her erection.

Practically drooling at this point, I wrapped my lips around her cock, completely engulfing it. I instantly started to deep throat, bobbing my head up and down and sucking hungrily. Holly moaned, arching her back and pushing deeper into my throat in the process. Unfortunately, my fiance was a bit too worked up and not really willing, to focus on foreplay at the moment. I had only been sucking on her cock for about a minute, before she flipped me over onto my stomach and yanked my boxers down to my ankles.

A hard smack on my ass and I chuckled, as she spread my cheeks and buried her face between them, shoving her tongue into my hole.

As she worked my ass with her tongue, Holly reached for the bottle of lube sitting on the nightstand. She applied a pretty big amount to my ass, before grabbing her cock with one hand and pushing right into me.

I gasped, gripping the sheets and moaned quite loudly as she quickly bottomed out. Both hands on either side of my head, Holly began thrusting in and out, fucking my ass hard and fast. The bed creaked underneath of us and I felt her tits, pressing against my back. I gasped again, then let out a low grunt, as she grabbed my hips and pulled me up onto my knees.

Slamming in and out of my hole, she reached around and grabbed my cock and started jerking furiously. My moans started getting much louder now, as I felt my ass clenching around her throbbing member. Holly was panting and breathing heavier and heavier now, her cock swelling up inside of me and sweat trickling down her forehead...she was so close. I buried my face in the pillow and shoved my ass back against her, hard, then feeling her cock surge and begin to pulsate deep within my asshole.

"Holy fuck!" she cried, in pleasure.

Her body began to shake and she exploded, as I continued grinding my ass against her and milking her cock dry. Seconds later, my own dick began to pulsate and sprayed a thick load of cum, all over the bed sheets underneath of me.

I collapsed, Holly's cock slipping out of my ass and she dropped onto the mattress, right beside me. With a low groan, I turned over and kissed her on the lips, before pulling her into my arms.

"I wonder if your cousin's ass feels as good as yours?"

I perked my head up and gave her a serious look, to which Holly started laughing and kissed me again. "I'm joking...let's save it for Kendra, shall we?"

"You better be joking," I laughed.

Rob picked us up at my place around 5:00, the day of the bachelor party. Like Holly, this was the first time that Rob was meeting my cousin, and they seemed to be getting along pretty well from the start. Riding shotgun, I asked Rob as we pulled out of the driveway, what the plans were.

"Sorry buddy," he answered, with a grin. "Can't spoil the night."

"C'mon dude, you know I don't want anything too wild!"

"It's cool," he laughed.

"Holly already gave me permission to do WHATEVER I want for you, tonight. Turns out, there are a couple of girls at the club you hooked up with in the past, that want one last go at ya before you tie the knot."

"Are you serious? And Holly is actually okay with that..."

"You know how she is," Rob chuckled.

"Besides, I think her and Annie are going to be spending the night with Lisa tonight. You know they'll be having plenty of fun themselves, if that's the case."

"You have one awesome fiance," Ryan said from the back seat.

We all started laughing, as Rob pulled the rest of the way out of the driveway and started driving towards The Raven; at least, I thought we were going to The Raven. As it turns out, Rob had something else in mind for the big night. Instead of going to the club, my good friend had rented out a suite at a very big hotel and we would be holding the party there. An entire room all to ourselves, it came with three bedrooms and a massive bathroom.

Along the way, we stopped at the beer distributor and loaded up on a few cases. Then it was off to the liquor store, to pick up the hard stuff and from there, we were on our way to the destination.

When we arrived at the hotel, I was surprised to see the actual room. Rob told me it was a lot of money but actually seeing it in person...I could only imagine how much he'd spent. There were already a few other people there and I immediately knew, who he was talking about when he mentioned the girls who wanted to "have some fun" with me.

The first person I saw upon entering the room, was none other then Christy.

"There's the groom!" She shouted, overjoyed to see me.

"Oh shit, it's been a long time!"

We embraced each other in a nice hug, laughing as she gave me a peck on the cheek.

"You're getting married, I can't believe this. I'm so happy for you and Holly and I cannot wait to watch you two make things official."

"I'm glad to hear you say that," I smiled.

"I hope you don't mind," Christy said, with a sexy grin.

"I talked to Holly and she said it's totally fine, if we have a little fun tonight. Only if you're okay with it though. I'm not going to be pushy or anything, if it's not what you want to do."

"I'm glad to hear you say that," I smiled.

"Let's just take it slow and...see where the night takes us."

We agreed on that much and made our way into the hotel room, cracking a few beers as more people soon arrived. About half an hour after we got there, I decided to pull Rob aside and tell him about my cousin. He was the only one who did not know that Ryan was into the same type of girl as we were, and I wanted him to help me set my cousin up as I had promised. Rob was as surprised as me and Holly both were, when I finally told him.

"You're serious?"

"Absolutely! He told me the other day, when he first got to town. That's why he's been single for so long, I think."

"Damn Jay; I never knew your family had so many trans lovers."

"Neither did I," I said, with a laugh.

"Listen...I want to set him up with someone tonight. What do you think?"

Rob looked around at the crowd; there were plenty of attractive women, who had shown up for this party. Any one of them would have been a good choice for Ryan, as far as I was concerned. I was asking Rob though, because there were a few unfamiliar faces and I didn't want to set Ryan up with anyone I hadn't already met.

Rob continued looking around for a moment, then stopped and looked at me. He hesitated for a few moments and started laughing hysterically, out of nowhere.

"What the fuck is so funny?"

"It's nothing," he said, trying to get a hold of himself. "Just...I think your cousin already found someone."

Rob pointed across the room and my eyes went wide!

Ryan was standing near the balcony, talking to none other then Kendra. "Fuck..."

I had mentioned the idea of setting him up with Kendra but, it had really just been a joke. In reality, Holly was right...Kendra wasn't the right person for a first timer like Ryan. She would DEFINITELY split him in half. Grabbing a fresh beer, I pushed my way through the crowd towards Ryan and Kendra, hoping that I could break this up before it went too far.

"Kendra!"

"Oh there you are Jay baby, how are you?"

She turned away from Ryan and gave me a huge hug, and a kiss on the cheek...and a smack on the ass of course.

"I'm glad you could make it," I said, hugging her back.

"I see you've met my cousin?"

"Indeed I have," Kendra said, backing up next to Ryan and smacking his ass.

Ryan jumped in surprise and blushed furiously, smiling nervously at me.

"Jay, you been holding out on me! How come you never told me, you had such a cute cousin?"

"I don't live very close," Ryan chimed in. "I'm just in town for the wedding but, I live in Florida."

"Well ain't that a shame? I might have to pay you a visit out there sometime, if you're down for it sugar."

I couldn't help but laugh, seeing how red Ryan's cheeks were at the moment. Kendra wandered off to the kitchen to get herself a drink, so I took that time to grab Ryan by the arm and pull him outside onto the balcony...I had to at least warn him about Kendra.

"Listen dude...you need to know, Kendra is a great girl."

"She's so fucking hot, too!"

Oh boy...

"Right...she is, don't get me wrong."

"So what's the problem? You don't seem to thrilled about me talking to her, for some reason. What's going on?"

"It's just...well...Kendra is a...big girl."

Judging by the look on his face, Ryan wasn't quite getting what I meant. I looked at him long and hard and he stared right back, then his eyes went wide and he started laughing nervously. "You...you mean..."

"Yeah...she's huge. Definitely not the best choice, if you've never been fucked before. I just wanted to warn you before you find out for yourself, so that you-"

"Thanks for the heads up," Ryan said, cutting me off.

I was surprised to see, he didn't look too scared.

"I think I can handle it though."

I couldn't help but laugh, taking a swig of my beer and shaking my head. "Alright then...don't say I didn't warn you."

I stepped back into the room and over towards Rob, who was waiting for me to tell him whether or not things were going to happen with Ryan and Kendra. "So?"

"He says, he can handle her."

"Aha! Oh man, your cousin has some real balls!"

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