tagTransgender & CrossdressersJay's Sex Club Adventures Ch. 12

Jay's Sex Club Adventures Ch. 12


I have had a LOT of technical errors lately, this was written a week ago and was edited four days ago and I just now submitted it. Hopefully things run more smoothly from here.

Those of you who have been hinting at Jay and Rob, I'm sure you will enjoy this chapter. I'm going to take a short break and put out a few one-shots that I have had in mind lately, and then I will be right back to working on Jay.

More to cum soon,


It was finally the day of our big New Year's Eve party, the end of 2013 was here at last. Lisa, Holly and I were throwing a big party at our apartment of course, and a lot of our friends were going to be there.

With a few people both from the club, and outside the club, but naturally the main crowd would consist of Rob, Annie, and Jen.

I woke early the morning of December 31st, and got out of bed to start preparing myself for the day ahead of me. I had a lot of stuff that needed to be done, and so did the girls, but I would be the one running around in the car doing all the errands. I wanted to get started as early as possible so that the party wouldn't start before I made it home. I quickly took a shower, threw on some clothes, and out the door I went.

The first stop was the grocery store to pick up plastic cups for beer pong. I also picked up a couple cases of water so people could stay hydrated after their drinking was finished. I grabbed plenty of stuff from the bakery section, and after paying for everything I made my way to Rob and Annie's place to pick up Rob. We agreed to meet early, so that he could help me take care of all the shopping for the alcohol, and also to help carry in all of the things that I would be purchasing.

I arrived at Rob's house and after leaning on the horn briefly, my friend emerged from his front door and climbed into the passenger seat.

"Happy fucking new year buddy," he greeted me with a big grin.

"Same goes to you... but it's not the new year yet."

"Hey, cut me a break, I'm pumped for tonight."

Rob always got like that when it came to our parties. This was partly due to the alcohol, but not entirely. Obviously, our parties all consisted of sex as well as drinking and it was at our get together that Annie was okay with Rob having fun with other girls... sometimes, the only condition was that he allow her to be a part of it as well.

"So... you and Annie got your eyes set on anyone yet for tonight?"

"Yeah... well she does," he said nodding his head,

"Annie wants another chance to hook up with you.

Go figure, I guess she really likes you."

I couldn't help but laugh and he gave me a light punch in the arm, shaking his head and laughing as well.

"Or maybe it's just that ass of yours... I'm submissive, but you're a little more into it than I am. I don't mind, I trust the both of you."

"I don't know how this is going to play out," I said sounding a little nervous.

"What... what are you talking about?"

"Tonight I mean, I might have my hands full if Annie's joining in. I mean, obviously, I'm going to be having my own fun with Lisa and Holly."

Rob chuckled, and I knew he was going to start making fun of me now.

"You're ass is going to be sore as shit tomorrow," he teased, "Those three are going to tag team you and you're probably just going to be one gaping hole by the time everything's all said and done. You do realize that, right?"

"Yeah, well that's my point, god, maybe I should buy some extra lube too."

With that said, Rob busted out laughing and I joined in a little too. But I stopped off at the drug store anyway, showing him that while I was laughing, I also was very serious about needing extra lubrication. After we picked up a large bottle of Astroglide, we made our way to the beer distributor. Three cases of beer later, we were back on the road... this time, heading towards the liquor store to buy some hard liquor.

As expected, Rob grabbed his usual bottle of Jack Daniels, and also a bottle of Jager. I snatched a bottle of rum and some vodka at Holly's request and a small bottle of Wine that Lisa had asked me to grab.

Once we paid for everything I drove us back to my apartment, carrying in the cases of beer and the bottles of hard liquor. Lisa and Holly were busy cleaning the entire apartment from top to bottom, even though we hadn't been living there for very long, those two girls were total neat freaks and wanted everything spotless. Luckily for them, Annie wasn't much different, so she was coming over a few hours early to assist with cleaning duties.

After we had everything put away, Rob and I stepped out onto the balcony and my friend lit up a cigarette. We thought we'd catch a half hour break, before heading back out to grab the remaining things we needed.

"So Jay... let me ask you a question..."

"Huh? Sure, what's up?"

"Well, you remember the last time you and Annie fucked, right?"

"Yeah... what about it?"

"Then you remember what I said... right?"

I tried to recall what Rob was talking about... that night was a little blurry to me really, and it had also been quite a while ago now. I vaguely recalled him standing in the doorway to the bedroom after Annie had finished pounding me good, and then slowly it came back to me.

"Yeah... I think so. Something about... getting a piece of my ass?"

Rob nodded his head, taking a drag of the cigarette and leaning back against the railing. I remembered we had talked about it later when we were both sober, and decided that we would leave it open for discussion in the future.

We never said yes or no, but then we'd never discussed it further like we had agreed that we would. Was that what he wanted to do right now? Talk further about the drunken suggestion he had made?

"I was wondering if... well, I don't know. Would you mind me joining in when you and Annie get it on tonight?"

I laughed at how outright he was about it and ran a hand through my hair while contemplating my answer. To be totally honest, I wasn't sure if that was something I wanted to do. I had become a pretty big bottom when it came to hooking up with Shemales, but they were still women to me... they just happened to have something a little extra. I never really thought about being with a man though.

It wasn't like I stopped and looked at guys and thought about how they looked hot or anything like that. Don't get me wrong, Rob's not a bad looking guy... I just didn't really know whether or not I wanted to have sex with a male friend. Then, I thought about it a little more, and it was just sex really.

A cock is a cock, and whether it's attached to a manly man or a hot chick with big boobs... it was just the thought, really.

"I guess... maybe. I don't know dude, I mean I kinda-"

"I get it," he cut me off, "Your nervous... that's cool, I mean, so am I... sort of. But then, Annie and the girls will be there so... It doesn't have to be awkward or anything like that. Maybe I could jump in, midway through, and it might help transition the whole thing or something."

He had a point. With the alcohol in our systems, the sexual energy in the air, maybe things would seem a little less strange when it actually happened. In a sense though, it almost seemed like Rob wanted to hook up with me a little more than I wanted to hook up with him... not that I was one hundred percent against it, it's just I hadn't really thought about it since that night and it seemed like he had plenty of time to think on it.

"So um... why? How come you're so anxious to hook up with me dude?"

"Hah," he chuckled, "Because you're so cute!"

I knew he was busting my balls now, and I stood up and gave him a playful shove, the signature move that he usually pulled on me.

"Seriously man, why the sudden interest?"

"I don't know... honestly, I'm all about new experiences. I really just love sex, with girls, girls with dicks... maybe even guys too. But Jay... I won't know until I try. I figured you're sort of the same way, so maybe you would like to try it too."

I took a deep breath and exhaled, leaning back against the railing and weighing it over a little further in my mind. What the hell, I thought... I'd already become a little less than straight at this point. Like Rob said, it was nice to experience new things and keep an open mind.

"Okay," I said finally, "You can join in, if you want to."

"Seriously... you'll be cool with it?"

"Hah! Yeah Rob, I'm serious. I mean hell, Annie is your girl anyway, so who the hell am I to say no if you want to be a part of it, right?"

"That's a good point."

"Listen, I just have one condition," I said.

"Let's not make this shit weird or anything when it's over with. I mean, even if I get into it...don't go thinking we're going to be a-"

"Come on dude," he laughed, "You're over reacting now Jay. It's just sex... remember I said that, okay? It's just sex."

I relaxed, and pushed away from the railing, nodding my head in agreement. Rob gave me a pat on the back and I walked back into the apartment to use the bathroom before we would head out to get the rest of the stuff for tonight. In the kitchen, Holly and Lisa were sitting at the table having a couple glasses of water when I came out of the bathroom.

"What's up Jay," Lisa asked. "Heading out again?"

"Yeah, in a few minutes."

"You and Rob sure were having a long conversation," Holly teased with a knowing grin.

"Yeah, yeah, I get the point, you know what's up. Looks like we'll be kicking off the new year with a bit of an orgy between all of us."

"By ALL of us you mean-"

"Me, you, Lisa, Rob and Annie."

"Sounds like one hot ass fucking night," Lisa joked.

As the two girls started joking and talking about how much fun it was going to be tonight, I grabbed my car keys and made my way back out to the car to finish up my errands with Rob. To avoid any uneasiness, we avoided the topic of what was probably going to happen between us tonight, and focused on the tasks at hand and just being friends.

We'd made it back with everything by about 7:00, Annie and Jen were there, and even though the party had yet to begin, it didn't take more than an hour for all of the other guests to arrive and get it officially 'kicked off'.

One familiar face I was happy to see, was Claudia. She was one of the first girls I had hooked up with at The Raven besides Holly and Lisa and it was definitely good to have her here at our New Year's party.

"Thanks for inviting me Jay," she smiled, giving me a warm hug.

"It's no problem, we're glad you could make it over."

"You have a really nice apartment," she complimented.

"Thanks," I said, "I have two really nice roommates too," I motioned towards Lisa and Holly, and Claudia chuckled.

"I am glad to see you happy Jay. I heard you've become quite the little cock sucker though. I have to say, I didn't see that one coming."

"Hah, yeah, well I still enjoy being a top."

"Maybe sometime you can show me if you still have it in you."

"I'd love that," I smiled. Our flirting over with, Claudia made her way out to the kitchen to grab something to drink, while glancing over her shoulder back at me with a seductive grin.

I cracked open a beer and Lisa started up the music. Everyone was talking, laughing, dancing around the apartment and having a really good time. It would definitely be a great night. Plenty of food and beer, and the food was really great too.

It was around 10:30 when I noticed a few of our guests were starting to get pretty intimate with each other. It didn't bother me, but the more I noticed people hanging all over each other, and clothes coming off of people, the more I started to wonder... Was this a New Year's party, or just a straight up sex party?

Again, it didn't bother me... it just didn't seem like we had realized what we were REALLY planning for tonight.

I wandered out into the kitchen, grabbing another beer and snatching some chips from the bag when Lisa came up behind me and gave me a slap on the ass and a kiss on the neck.

"Hey there," she said happily.

"Hey yourself! You having a good night?"

"It's great," she replied. "Rob and Annie are already going at it, and Jen is out there getting it on with some guy named Chris."

"Well, what about you?"

"Me; what about me?"

I sat down at the kitchen table, taking a swig of beer to wash down the chips I had been eating for the last few minutes. "Got your eyes on anyone tonight?"

"I don't know," she smirked, "Obviously I'm waiting for our time alone... but are you hinting that I could get a sort of 'warm up' with somebody else of my choice?"

I was surprised she even had to ask, I thought we had a no strings attached thing going here. I wasn't going to cling to her and come off seeming possessive or anything that might disturb her or piss her off at me. "If you want to, then I don't mind... I thought that was a given?"

"That's true, what about you?"

"Me, well...I don't know."

"Oh come on, Claudia's had her eyes on you since she got here. You two hooked up once before, didn't you?"

"Yeah," I laughed, "She made it pretty clear to me earlier that she would like another shot at me too."

Lisa grabbed my hand, pulled me out of the chair and gave me a push in Claudia's direction. I laughed as I stumbled across the kitchen, in her direction and she giggled as I stopped in front of her.

"Hey," I said, rubbing the back of my head.

"Hey there... wanna have some fun?"

I gave no reply, just took her hand and led her out of the kitchen and into the living room. Just as Lisa had said, Rob and Annie were already sprawled across the floor in the 69 position with Annie on top. Just watching the two of them together was getting me turned on, and I sat down on the couch, pulling Claudia on top of me.

We smiled, excited to be with each other again, and as she draped her arms around my neck, she leaned in and kissed me. As I kissed back, her hands were instantly roaming all over me and making their way down south towards my groin.

It did not take long before she had slid down onto her knees, unzipping my pants and freeing my cock, swallowing it whole. I watched as her head moved up and down, her lips gliding over my cock and that's when I saw Holly across the room.

I could tell she was a little tipsy, but not too far gone just yet. She seemed to glide across the room, slipping out of her pants and undergarments as she moved and stopped right alongside Claudia and myself. I didn't say a word, neither did she and neither did Claudia. Holly stroked her cock next to Claudia, and the girl released my dick from her mouth and started sucking Holly.

She moved back and forth between Holly and me, and somewhere along the line, I slipped out from underneath of her and got on my knees behind her.

I pulled her pants and panties down, exposing her beautiful ass and her balls dangling between her legs. As she focused on sucking Holly's cock, I started to fondle her well hung package from behind her. I pulled her legs back a little, parting them slightly so I had better access to what I wanted.

I started sucking her cock from behind, while she continued sucking Holly. I sucked her dick, while rubbing her balls with one hand and after a minute I moved from her raging hard-on to her beautiful asshole. Licking up her balls towards her ass crack, I started teasing her hole with my tongue, lubing her up with saliva. She moaned, deep throating Holly as my tongue pushed into her hole, thrusting in and out.

"Oh shit," she sighed, releasing Holly just long enough to speak.

Now was the time; my own dick had gotten so hard by this point, I could wait no longer. I got up behind her, giving her a smack across her ass before positioning my tool at her entrance. She stayed focused on Holly while I gently probed her for a few moments before pushing right into her.

"Ohhh fuck!"

The sound of her soft moans filled my ears, and I wasted no time, immediately pounding her ass with long hard strokes. Holly laughed, as Claudia tried to focus on sucking her dick but it wasn't all that easy with me behind her fucking her in the ass at the same time.

Eventually, Holly moved away from her and stood up alongside me, shoving her dick in my mouth.

"Since she can't focus, you can finish what she started... sound good?"

"Mmff," I said, with my mouth full of her big fat dick.

I drove my dick harder and deeper into Claudia's asshole, pushing her forward so that her face was buried in the couch cushion and her moaning was muffled. Holly grabbed my head, and started thrusting down my throat, her balls pressing against my chin. I felt myself getting closer, the combination of me buried deep in Claudia's warm asshole and Holly's dick crammed down my throat was more than enough to throw me over the edge.

I moaned loudly, sending vibrations over Holly's shaft, as my cock erupted inside of Claudia, pumping her full of my semen. At just about the same time, Holly cried out in pleasure, spraying her load down my throat. I swallowed it all while still pushing gently in and out of Claudia for a few moments, before finally pulling out of her ass.

Holly leaned down to kiss me on the lips, and Claudia turned around to face me. She started licking and kissing me all over my chest as I made out with Holly, and eventually I had to part lips with her so that I could pull Claudia into an equally passionate kiss. I lifted her up and laid her down across the floor, kissing my way down her chest towards her lower regions.

"Oh shit, Jay... what are you-"

I cut her off, wrapping my lips around her dick and starting to suck. I didn't remember doing this with Claudia our last time together, and I figured since I came and so did Holly and she didn't, this would be a good way to finish getting her off.

"Oh fuck," she sighed. "You really ARE good at this!"

"I know... right?" Holly laughed.

No sooner than Holly finished laughing, did Claudia cry out in pleasure, grabbing my head and forcing it down further over her cock. She arched her back and exploded and I felt the warm sticky flow of her cum, firing down my gullet.

I licked her clean, licking even her balls and then moving back up to kiss her again. Her tongue pushed into my mouth, and she tasted herself on my breath.

"I don't get very many guys who like to suck me off," she said, after the kiss finally broke.

"So thank you for that; it felt great."

"I'm glad you thought so."

We were interrupted by someone moaning, quite loudly, and I glanced over to the left to see that it was Rob, fucking Annie from behind. Claudia got up to go to the bathroom, and it was just Holly and I for now. I glanced across the room and caught sight of something I hadn't expected to see, and for some reason it made my stomach turn... it was Lisa. She was making out with some guy, wrapped tightly in his arms.

They were really intense, and I don't know why, but I suddenly felt rather... sick.

"You okay," Holly asked.

"Yeah... I uh... just noticed how hot and heavy Lisa and her new friend are."

"Oh," she said, disappointedly. "Yeah, that's Mike. They just started hanging out a few weeks ago, I'm shocked she didn't tell you."

So now she was hanging with other guys, not saying a word to me... we had an agreement yeah, but I was a little shocked I never heard about this guy at least.

"Whatever... it's just sex," I said, remembering Rob's words and shrugging it off.

"Yeah, she says so but... I think she's lying."

I glanced over at Holly, confused, and saw that she looked a little saddened by her own words.

"Lisa swears it's just sex with this guy like it is with you but, I think she has feelings for him."

I could see that, in how attached to the damn hip she was with this dude. Hell, I couldn't lie... I really liked Lisa. I had hoped that someday when we both grew out of this whole "experimental" stage, maybe we could be something more than just friends with benefits. Now, I wasn't sure anymore.

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byWhiskeyIsGood© 26 comments/ 33435 views/ 36 favorites

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