Jay's Sex Club Adventures Ch. 01

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Jay's friend introduces him to a whole new world of fun.
7.7k words
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Part 1 of the 25 part series

Updated 06/08/2023
Created 12/08/2013
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Summer 2013, I turned 25 years old. I will not lie and say that I was thrilled or anything like that, to be honest with you, it was quite the opposite. I was not happy in the least bit to be just another year older, as I liked to say. Especially given the fact that at the midway point of my twenties, I still had been unable to find a woman that I could develop a meaningful relationship with.

I'd never, ever, had any real luck with women since I had first started dating when I was thirteen years old... I had been in one relationship after another. Some of them just went sour, some of them had no real chemistry, and then there were the few in which I had been cheated on... like my most recent one with a girl named Nikki.

Maybe, that was what had me so depressed in the first place... see, I had only found out about Nikki cheating on me just a few short days before my 25th birthday and we had been dating for a year. I liked to say that I had actually been in love with her, it was the first time in a long time that I had felt like I could trust a woman. Look where that got me.

So needless to say, I wasn't quite looking forward to spending my birthday alone. My parents, seeing as I was older now, were obviously not going to throw a party for me. They invited me to dinner, gave me a card and bought me a cake and that was really about all there was to that. My depression had sort of brought me down to a level where I had very few friends anymore, so there was not anyone I could spend it with just hanging out.

All I really had was work and then home to have dinner and maybe crack open a couple of beers. I guess a part of me was almost content with that.

Then, I got a text message from someone I had not spoken with in a little over a year... his name was Rob. Rob and I had been friends since we were ten years old in elementary school. He was the oldest friendship I had in my life, and we had always been in and out of contact with each other over the years but we always remained friends regardless.

Hearing from him after a year of not talking for no real reason, actually seemed to lighten my mood a bit. I smiled as I opened the message and it read, "Happy birthday dude! What are you up to tonight?"

"Thanks man. Probably nothing, not feeling up to anything big this year," I messaged back.

"Man, give me a call, let's talk." He must have been watching for messages as he returned mine almost immediately.

Sighing, I went into the phone book and clicked his name, dialing the number. After a couple brief rings, Rob answered the other end.

"Hey what's going on bro, it's been so long."

"Yeah, I know dude. What're you up to?" I asked.

"Not much man, listen, you staying in all night on your birthday?"

I hesitated, taking a swig of the beer I had in my hand and leaning my head back against the cushioned recliner.

"Yeah dude... I'm feeling pretty down."

"What's wrong?" He quietly asked.

"It's just... I don't know man. I'm sick of women, is all I suppose."

"Nikki broke up with you didn't she?"

He knew... he always seemed to know. After all, he had known me half of our lives, so I expected he would. Rob always had good luck with women, while I always had shit luck. He tried to help me out quite a few times. It was never his fault that it never worked, he tried, and it was all on me for some reason. I was the one who had apparently been cursed and that was not his fault.

"Yeah, I don't know what's wrong with me man."

"Nothing's wrong dude," he replied. "Listen... why don't we get together and have a few drinks tonight man? Beats staying home on-"

"I don't know dude," I interrupted him, "I'm not feeling up to it really."

"Oh c'mon Jay, don't beat yourself up like this. Tell you what... you really don't want to go anywhere? Let me come over there, I'll bring a couple six packs and we'll have a great time."

I saw no problem with that, what was the harm really? At least this way, I would not have to deal with people or the general public and I would be able to hang out with an old friend and maybe it would cheer me up.

"Yeah sure... come on over," I agreed.

"Great, I'll be there in about half an hour."

We hung up, and I pushed myself up out of the recliner and started tidying up the apartment a little while I waited for him to arrive. About an hour passed before I heard a loud knock at the apartment door, and I went to unlock and open the door. I pulled it open to see Rob standing there with two six packs as promised, and that same old lopsided grin he always had.

We gave each other a handshake and brief hug, before I led him into the apartment and shut the door behind us, then we both took a seat at the kitchen table. We ordered a pizza and split it along with the two six packs he brought with him, and we started catching up on missed time.

I told him about Nikki and how I caught her with her apparent ex-boyfriend. I told him how she had really felt no sort of remorse or anything like that...it really fucked me up, but he could see that clearly without me having to tell him. As we started to feel the effects of the alcohol, we swayed from what I viewed as depressing talk. When I would drink, I was usually more cheerful and I started wanting to talk about happier things the more I felt it kicking in.

I told him about the new job that I'd had for a few months now, and how it was really working out well. He asked about my family and how everyone was doing, and I went on to ask the same questions in return. Somewhere along the line though, I guess I started to feel down again, and naturally, he picked up on it right away.

"Hey man, listen... don't sweat that Nikki bitch okay? Seriously, the time I met her she came off as a total bitch."

"Hah, you only met her once Rob."

"Sometimes it only takes one time to know a bitch," he slurred and we both laughed.

"Well I appreciate it Rob, but to be honest...you've always been the lucky one when it comes to women, and I don't mean any offense, but I don't think you understand how it feels to be twenty five years old and have zero luck with women."

"Ah, come on, don't be like that. I know what you are saying, I do, but let me tell you something not a lot of people know. The last three years... I wasn't doing so hot with dating."

That was a shocker, I thought silently. Rob not doing well with women? That was something I never thought I would hear.

"Well... why not?" I asked.

"To be honest... I don't really know. I do know what you are feeling. I didn't say a word about this to anyone until now, but a few years back this one chick I was seeing hooked up with someone else behind my back. Really fucked me up in the long run too, but I don't know. After that I was just not the same, I started going out and hooking up randomly and drinking a bit more."

I had never known any of this, it must have happened during one of those periods where he and I had not been in contact all that much. Rob had always been pretty good at keeping things from people when he wanted to, the complete opposite of me, who was the kind of person that you could read easily.

"It's all good now though, you know why?"

"Why's that," I asked curiously.

"Because it made me realize something... women are evil. But you can't really live without them right?"

"That's the old saying, yeah," I said laughing.

"Yes, it is, but what if I told you I found a way around that? I found someone else man... I found someone I actually love, and hell, she's my best friend."

Holy shit, I thought to myself. Rob just admitted he had fallen in love with someone? Now that was definitely something I did not see coming.

"That's awesome dude! What's her name?"

"Her name is Annie. She's fucking hot as hell too dude. But I'll let you in on another secret here," he said slurring his words.

He was clearly a bit more drunk than I was, so I was not sure whether to take whatever he said next seriously or not, but I laughed and listened as he continued on.

"What if I told you," he slurred. "That there is a whole different breed of women out there... that can rock your fucking world, like it has never been rocked before. Annie is one of them, and I can tell you, she is living fucking proof. Man, I can introduce you to some people who will make you forget all about Nikki and all those other bitches faster than you can blink."

I was pretty sure it was the alcohol talking, I started laughing hysterically.

"No, no, dude I'm serious," he said laughing with me.

"Oh come on Rob, a girl is a girl right? You're not making much sense."

"No, listen man... here, look," he pulled out his cell phone. A few seconds later, he was showing me a picture of a beautiful blonde wearing a sexy blue dress.

He showed me another of the same girl, only in this one she had her arms around Rob from the back and her chin resting on his shoulder as he held up the phone to snap the photo.

"This is Annie," he said laughing, "Ain't she fucking gold man?"

"She's pretty cute," I replied honestly.

"Right," he looked at me earnestly, "now what if I told you, I met her somewhere that doesn't cater to your average women."

I was really having a hard time trying to figure out where he was going with all of this, but I laughed and listened on.

"I met Annie at a Transsexual club man, she's a tranny."

"No fucking way," I blurted out laughing at him.

Now I really was pretty sure it was just the alcohol talking. There was no way Annie was a transsexual. She looked hot as hell, much like he had described her, and I could not see any reason to believe she was actually a man. He had to be fucking around with me or some shit.

"I'm serious!"

"No you're fucking not, quit joking."

"No, really, here look," he handed me the phone again and my eyes went wide. The next photo he showed me was one of Annie lying sprawled out across his bed, completely naked, legs spread wide apart... and to my surprise, standing straight up from where there should have been a pussy, was a huge, throbbing cock.

It had to be at least eight inches long and it was completely erect and holy shit I was in a state of shock. I had to take a very long swig of my beer before I could clear my head enough to say anything after that. Rob was waiting for me to speak, a huge lopsided grin on his face and he looked like he was ready to laugh at me and my reaction.

"Dude... what the fuck,"

That was the only thing I could bring myself to actually say at this point... what the fuck. Rob was definitely not gay, he had never once given me reason to believe while we were growing up that he was gay. And yet here he was telling me about this hot ass girl he was fucking and then showing me a picture of her and I find out she has a dick. What sense did any of this make? Zero in my opinion, but I believed him now

"Holy shit... that's real? Like you didn't Photoshop it or anything?"

"No, it's completely real, she's a real transsexual."

"Wow... I mean... are you gay?"

"Fuck no," he laughed. "Look at her dude, that's not a man right? She looks like a woman, acts like a woman, smells like a woman, she even sounds like a woman. She gives better head then a woman though, and that's because she use to be a man and she knows what men like more than a genetic girl would know. She's all women she just happens to have something extra."

"That's... that's fucking crazy."

"I know right? And the best part? Anal sex all the time, do you know how many genetic girls I dated that were willing to have anal sex with me, only one. With a girl like Annie, anal sex is a fucking given."

He had me laughing again, and I finished off my last beer and stood, my legs shaking beneath me as the room spun just a little. I still had a lot of trouble taking all of this in though, and I had a LOT of questions to ask him.

"So like... do you like... do you always GIVE anal sex to her... or so like, do you take it from her too?"

"Hah, hah, nah man, that's not for me, some of the guys at the club like it but it's not my style.

Annie would be willing to do it if I were interested, but we never bother. But listen man, you should come check this place out with me."

"Nah, I'll pass," I replied staggering to the kitchen.

"Oh, come on, it'll be fun! You'll love it, I swear. I'm telling you, there is no women like a women with a cock Jay, you will love it I promise."

"I don't know... I mean... what if she wants to like... bend me over and stuff?"

Rob started laughing, quite loudly I might add, and I started with him. He stood up from the table, almost knocking over the chair and stumbling out behind me giving me a hard pat on the back.

"There's all sorts of them there... some like that stuff, some don't. But I mean even the ones who do like it, they aren't pushy about that. If you find a girl who wants it and you want it too, that's great, if you find a girl who wants it and you don't nine out of ten times they are pretty respectful. No one's going to make you do anything you don't want to do."

Maybe it was the beer, but I was actually considering checking this place out. I wasn't quite sure why, but for some reason I was interested. Maybe it was the fact that he had stressed how much better these women were at making a man feel good then genetic women. But then if he had only been with one of them, how could he honestly say that it wasn't just him being lucky... like always.

"How do you know their all so great, if you've only been with Annie?"

"Only been with Annie? No, I never said that. I was with a couple different ones before Annie. Two or three actually, and they were all great, it's just Annie is my one and only, that's all."

Okay... so maybe he had enough experience to say for sure. Now, I was really starting to consider this. "Alright, fine," I said finally,

"I'll go."

"Great, that's awesome, I promise you're going to love this place," he exclaimed excitedly.

"Listen, me and Annie will be there this Friday night, come on down and I'll take care of you man, I'll find you a real sweet girl."

We talked a little while longer and finally around 12:30 or so Rob left and I locked up the apartment before stripping down to my boxers and climbing into bed. I sighed, staring up at the ceiling, thinking about everything that Rob had told me tonight, and I hoped he was right. I hoped this turned out to be worth it, because I was really wondering right now why I had said yes.

Friday came a lot faster then I was anticipating, and by that point, I had decided I was just going to check this place out just to satisfy my friend. There was no real doubt in my mind, I was not going to be attracted to anyone there enough to hook up and have sex with them but there was no reason not to go just to have fun. Plus if I did not at least show up I was pretty sure Rob would be a little irritated with me for it.

So Friday after work, I came home and showered, before throwing on a casual t-shirt and a pair of denim jeans along with my converse sneakers. At about 7:00 I was out the door and in my car heading to the place he had given me directions to, it was called The Raven.

When I got there, I parked my car right around the corner and walked up to find Rob waiting outside smoking a cigarette, and who else did I find with him? The lovely Annie, at his side, smiling and having a seemingly very happy conversation with a few friends. As I got closer, Rob noticed me instantly and waved me over.

"Hey, what's up, I knew you'd be here!"

"Yeah, I told you I would," I said and we shook hands. He looked over at Annie and her friends and smiled.

"This is my buddy Jay. We've known each other since we were kids."

"Nice to meet you Jay," his girlfriend said. "I'm Annie."

"Nice to meet you too. Rob's told me a lot about you."

"Oh he did, did he," she asked in a joking manner and shooting Rob a funny look.

"So, I guess you know my little secret right?"

"Uh... yeah... not quite so little though, is it?" I said trying to make a joke.

It seemed to work as Annie, Rob and a few of the others standing around started laughing and so did I of course. They all seemed nice enough, I thought, and I felt myself relaxing a little bit. Finally, we all went inside and I was impressed at what I saw for the most part.

It was a pretty big place, lots of room to move around. There were two large dance floors and two bars in between. There was also a balcony, with a third bar on it and an extra set of bathrooms... then there was the basement. Rob told me that this was not your ordinary club, it was, but there were many rules that were allowed to be broken that some places would not let be broken.

In other words, this was your typical club, but a lot of people had a habit of hooking up and having sex HERE instead of leaving together and having sex back at one of their homes. Apparently, it was completely acceptable because according to Rob and Annie, the basement area was dedicated to anyone looking to have sex.

There were private rooms in which a couple, or sometimes more than just a couple, could go to have fun. I wasn't that impressed by that.

Surprised yes, but I did not actually come here to hook up with anyone, so that part did not really interest me.

Looking around though, I noticed there were a lot of women here. But then I remembered what kind of a club this was, and I found myself wondering just how many of them were actually genetic women. I figured the amount was probably relatively low, considering this place catered mostly to transsexuals.

"Hey, come on let's go get you something to drink," Rob said dragging me over to the bar.

I sat down and he got me a beer, and we started talking normally as though we were just back at my place instead of in the middle of a transsexual club. After about half an hour, I noticed that despite what I had told myself prior to coming here, I could not seem to help but look around at my surroundings... and a part of me liked what I saw.

A large amount of these women did not look like men at all. Mostly all of them were very convincing. There was a large variety of them too, white, black, Spanish, a few Asian here and there... it was a place that seemed very friendly to everyone.

I took a swig of my beer as I noticed the familiar tightness in my pants, and I realized that I was having a harder time not being interested in this place then I had intended on having originally.

"Hey, Jay check it out," Rob said breaking my train of thought. I turned around to face Rob only to find him standing next to me with an extremely attractive girl at his side.

She was tall, maybe about an inch taller then I was. She had shoulder length red hair, piercing blue eyes and a gorgeous body. Her clothing left very little to the imagination, a short skirt and a top that showed off a beautiful amount of cleavage.

Cleavage that almost made me forget once again, that this was not your typical club.

"Jay, this is a friend of mine. Her name is Lisa. Lisa, this is my buddy Jay, we go way back to elementary school."

I realized then she was actually one of the same people who had been out front earlier when I first arrived with Annie. That meant they were probably friends. She smiled, extending her hand to shake mine.

"Nice to meet you," she said happily.

"Likewise," I replied.

"I'll uh... just leave you two alone for a bit," Rob said standing up and walking away. I sighed, smiling and shaking my head. I pulled out a seat next to me so she could sit down and she thanked me.

"So Jay, tell me, have you ever been to a place like this before?" she asked.

"No... no, uh... this is my first time actually."

"Really, a newbie huh... Rob brought you here,

didn't he?"

We both started laughing, it was not necessary for me to give an actual answer, it seemed like she already knew the answer was a yes. We started talking and getting to know one another and I bought her a few drinks and we talked some more and before long I felt like I was really getting along with her. Then she said,

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