Jay's Sex Club Adventures Ch. 01

"Why don't I show you around and introduce you to some other people, would you like that?"

What the hell, I figured finishing off the last of my drink.

"Sounds good to me," I said standing up. She took me by the hand and led me to the other side of the bar and started introducing me to people.

The first person I met was a girl about the same height as Lisa, with blonde hair and hazel eyes and a body just as sexy as Lisa's was. Her name was apparently Jen.

After I met Jen, Lisa introduced me to a warm welcoming smile named Leslie. She was a brunette with a firm handshake reminding me that she was not like other girl's and her voice was a little deeper than a girl too. Despite those few minor differences, Leslie was still pretty attractive herself.

Then, there was Holly, a girl with hot pink hair and a beautiful smile. She had long smooth legs, green eyes, and a voice of an angel. Her breasts were not that big, she was relatively flat chest actually, but that did not bother me.

"So are you having fun Jay," asked Holly.

"So far, so good," I replied honestly. It was the truth. I really was enjoying myself. Between Holly and Lisa, I was having a very nice conversation when I decided I had to take a quick trip to the bathroom. Before I left, Lisa grabbed my arm and pulled me to her and whispered in my ear,

"Hurry up, and I'll show you the basement when you get back."

I knew what that meant, because I knew what the basement was mainly for since Rob had told me all about that part already. That meant I had a decision to make. I had come here intending to have just a good time hanging out and meeting new people. Rob of course intended for me to hook up with someone from the start, but I had been unsure of that.

Now that I was here though, now that I had met all of these beautiful women... Lisa included... I was actually second guessing whether or not I wanted to spend my night just talking.

I walked to the bathroom, thinking about all of this as I walked, trying to make up my mind before I got back to where Lisa was standing with Holly waiting for me. I emptied my bladder, splashed some cold water on my face and stared at my reflection in the mirror for a moment.

"Now is the time Jay," I whispered to myself.

"What are you going to do? Make up your mind."

I pushed away from the sink and walked out of the bathroom, and as I did, a very tall and well-built looking deep dark-skinned woman came up from behind me and suddenly gave me a slap on the ass.

I jumped, obviously taken by surprise, and whirled around to face her. She grinned at me and spoke in a deep yet strangely feminine voice, "Fresh meat?"

"What?"

"You new here white boy?"

"Uh...y-yes," I replied nervously.

"Mm, I can see that. You got a nice ass though.

Anybody ever tell you that?" I gave no reply, and she giggled leaning in close to me. I could smell her perfume, and feel her hot breath on my neck as she pressed me up against the wall behind me.

Lisa's P.O.V.

I stayed with Holly and talked for a few minutes while Jay was in the bathroom. She seemed just as excited to have someone new here as I was, and we were having a good time talking about our new friend.

"He's really cute," Holly said.

"Oh god, I know, isn't he though? Such a cute butt too, Mm, I can't wait to get my hands on him."

"I bet you can't," she laughed. "But don't forget me, I want seconds."

"Hah, Hah, you'll get your turn don't worry, I think Jen wants in too."

We were both laughing and I was fantasizing about what it was going to be like when I finally hooked up with Jay, I could not wait.

"Do you think he'll be submissive?" Holly asked.

"I don't think so," I answered truthfully. I knew, full well that Jay was not interested in being penetrated, that was okay, I was a respectful enough person not to force him into anything he did not want to do.

But it was still nice to think about what it would be like, and damn did he have a fuck worthy ass.

"Uh-oh," Holly said, interrupting my thoughts.

"Looks like someone else has her eyes set on our new friend and his butt, and I doubt she's going to be as patient about it as you are Lisa."

I looked up to see what she was talking about, and immediately I saw Kendra, pinning Jay against the wall next to the bathrooms. Obviously, he did not look very comfortable, and I knew just by her gestures what she was trying to convince him to do. Kendra was someone who came to this club for one thing and one thing only... white men and their assholes.

"Shit, I guess I better go take care of this," I said anxiously.

"Yeah, I think that would be a good idea," Holly chuckled.

Jay's P.O.V.

My heart was racing in my chest as she ran her hands down my back and started rubbing my ass, squeezing it and massaging it. I was completely frozen.

"I really... really love virgin ass,"

"To bad," Lisa interrupted, "Cause he's all mine. We already had plans,"

The woman gave Lisa a dirty look and snickered, before backing away slowly and running her hands down my chest in the process.

"Maybe later then," she said before walking away.

I sighed, looked at Lisa and she started laughing at the look on my face.

"That was Kendra," said Lisa,

"She's one of the more strong willed divas in this place and she loves white boys more than anything. So watch out for her... unless your into that sort of thing."

"No, not really," I laughed nervously. "You really saved my ass back there, quite literally I mean."

We both laughed and she gave me a smack on the ass, making me jump.

"Well, I meant what I said too, I already got dibs on your anal cherry."

To that, I gave her a worrisome look and she looked back at me seriously for a few moments, before breaking into a fit of laughter once again.

"Don't worry Jay, I'm kidding. If you do not want to do that, then it's fine with me, I don't mind. You'll meet and possibly hook up with a lot of girls here and you're going to find that mostly all of them are very accepting and respectful, I promise you that much, okay?"

"Yeah... thanks,"

"No problem... now... how about I show you the basement like I said?"

"Sounds good to me."

Lisa took me by the hand and led me down the long spiraling staircase to the basement area. I was surprised to see how big it was down there. There was a long, wide-open hallway with doors on either side of the hall, the floors were marble, the lighting was a dimmed and there was plenty of dance music blasting through the stereo system.

We walked down the long hallway and as we did, I felt my heart beginning to speed up again, I wondered what was going to happen once we found a room.

We stopped just outside the last door all the way at the end of the hallway and Lisa smiled at me before she took hold of the doorknob, opening the door. She motioned for me to step inside, and I obeyed.

Once inside, I was met with a small comfortable looking room, the floors were still made of marble. The lighting was a little brighter, and there was a small love seat on one side of the room and a comfortable looking mattress for two with silk sheets on the opposite side.

"Take a seat," she motioned towards the loveseat.

I sat down slowly, sinking into the chair, it was extremely comfortable. But it did very little to calm my nerves I realized, as I began tapping my foot quite heavily and nervously. She smiled at me shutting and locking the door before moving closer.

For the first time I really saw just how beautiful she actually was, her whole body was incredible. She leaned in close, placing her hands on my knees and smiling. I could smell her sweet scent and I had a perfect view of her cleavage.

She had glitter sprinkled on her breasts and a little on her neck as well, and it made her look like she was sparkling in the light that shone upon us both.

"You want to have some fun baby?"

"I... I would love that,"

"Good... so would I... I'm going to rock your world!" Lisa exclaimed.

She straddled me, sitting on my lap facing me and started grinding against me with her arms wrapped around me. She was giving me a lap dance, and the feeling of her ass moving against my cock, even if it was through my pants, was a feeling I welcomed happily. I put aside all of my fears and went along with it excitedly.

Eventually, she turned around, her back facing me and continued grinding up against me. She leaned forward some, giving me a perfect view of her beautiful ass, it did not look like a man's ass at all, and that was for sure. She even let me touch her, and her cheeks were just as smooth as a real woman would be.

She went back to facing me, and then she closed the gap between us and I felt her soft, warm lips press against mine. Her tongue probed at my mouth, until I opened my lips granting her access. My tongue and hers were now locked in a wrestling match, our soft moans filled the room as we explored one another.

We broke the kiss and she went right for my neck, licking, sucking and kissing, leaving a very, obvious hickey in the place of her lips.

Eventually Lisa slid off of my lap nice and slow onto her knees between my legs. She started rubbing me through my jeans and I felt my cock stiffen even more than it already had. Slowly, she unzipped me and reaching inside, freed my throbbing erection from its restricting confines.

She took me in her grip, a very firm and perfect grip, moving her hand up and down the length of my shaft to start. With her other hand, she started massaging my balls and I sighed, leaning my head back and giving in to the wonderful feeling.

Up and down, she moved her hand, stroking me and playing with my balls, until finally I felt Lisa's warm wet tongue flicking the head of my shaft.

I jumped at first, but then groaned as she flicked it once again. Almost as though she were getting a taste test, she licked the head like it was a lollipop, and I absolutely loved the feeling of her work.

Finally, she took me in her mouth, and I was in heaven. Up and down her head bobbed, her warm wet lips gliding back and forth over my cock. She could deep throat like a true expert, gagging only a little. She took me all the way into her throat, and it felt as if she were trying to swallow, the muscles in her gullet massaged my cock and it was the best feeling in the world.

This had to be probably the best blowjob I had ever received,

She started working me a little faster now, and I could feel the old familiar feeling of pressure building up in my balls, she sensed it coming to. Just as I was about to unload, she stopped, and I looked down at her surprised and almost disappointed, and she simply smiled back up at me.

"Why... why'd you stop?"

"I wouldn't want you to cum to soon, now would I?"

I sighed, as I felt the pressure decreasing, and when she realized I had recovered, she went right back to sucking my cock again. She started out the same as before, moving slowly, working me up to that agonizing feeling of pressure, and then once more as I was about to blow... she stopped.

It was like torture, she had me right where she wanted me the whole time,

Finally, the torture stopped though when she stood up and reached for her purse. Out of her purse, she pulled a Lifestyle Condom, along with a bottle of Astro-Glide. If this meant what I thought it meant, then I was very happy that she had not made me cum too soon, because I was certain it would be great. I had never actually fucked a girl in the ass before, though I had always wanted to try it at some point.

None of the girls I had dated in the past were open to the mere suggestion, and so I had been forced to forget that desire...until now. Maybe Rob was right, maybe this was a very good thing indeed.

She slowly pulled her skirt down, along with her silk white panties and for the first time I actually got to see another cock besides my own, she was not actually very big to be honest. Maybe around six inches, although she wasn't one hundred percent hard yet, but it still was not such a bad sight.

As she started to kiss me though, I felt her cock responding, growing harder against me and when we broke apart and I looked down I was surprised to see she was a little bigger then I originally thought. She must have actually been about seven inches, pretty impressive really... but I still was not looking to do anything sexual towards her when it came to her cock.

"Don't worry about that," Lisa said motioning down to her member. "Like I said, nothing you don't want to do, you have my word."

"I trust you on that,"

"Good... I'm glad. Now, let's have some real fun."

She handed me the condom and I tore open the package, unrolling the latex over my hard cock while she poured a glob of lube into the palm of her hand and reached behind her to smear it all over her asshole. She turned around to face me, giving me a good view of her ass.

She bent over some, spreading her cheeks with one hand and let me watch as she smeared the lube all over her hole. She inserted a finger into her ass, and started fingering herself.

After a minute, I watched as she carefully inserted a second, and a few minutes later, she had worked at third one into her hole. My cock was as hard as a rock at this point, watching her slide her fingers in and out of her wet asshole, glistening with lube.

She pulled them out finally, and applied an extra amount before handing me the bottle.

"Put some on just for good measure," she said motioning towards my cock. I got the hint, and poured some over my shaft, rubbing it in real good. The condom already had lube on it, but a little extra would not hurt I figured.

When we were both ready, Lisa stepped forward and once again straddled me, sitting down towards me. I felt my cock probing at her asshole as she draped her arms over my shoulders and kissed me passionately.

As we kissed, I felt her pushing down on to me, and then I felt myself glide right into her. God she was so fucking tight! I moaned into her kiss and she reacted with a similar sound to my own.

My hands moved down from her breasts to her hips, taking hold of her love handles and holding on tightly as she started to ride me. She moved up and down on my hard cock, sliding in and out of her hole, leaning in closer to me. I took in the sweet scent of this beautiful girl, loving every second of what we were doing.

I could feel her own throbbing erection mashed between our bodies against my stomach, it was an odd feeling, but I overlooked it.

After a few minutes, she lifted herself off of me, turning around as she bent over, and I stood up behind her. I took hold of her hips again, pushing my cock right back into her gaping hole and continued to pound her with long hard strokes.

Standing up now, she was moaning louder, her cock swinging back and forth between her legs with every thrust and her breasts jiggling each time I slammed into her. Something came over me, and I found myself reaching around and taking her erection in my hand. I gave it a firm squeeze and she practically cried out in pleasure.

I pushed deep into her and squeezed her cock at the same time, and I loved the reaction I got. Lisa's body seemed to tremble beneath me, and her anal muscles clenched my dick tighter.

"Oh, fuck Jay, fuck yeah... fuck me harder!"

I was not going to say no to that, so I started ramming in and out of her, pumping her cock in rhythm with my thrusts. We were both panting, breathing heavy, sweating and moaning. The smell of sex filled the room. I could feel myself building up to what was sure to be a very intense orgasm. I could feel her dick starting to pulsate in my hand and I knew she was just as close as I was getting.

I pulled out, threw her on to the mattress in the corner of the room and climbed onto the bed with her.

I lifted her legs, wrapped them around me and pushed straight back into her. In missionary now, I pounded her ass as hard as I could with every bit of strength I had in me. The bed shook beneath us, and we both started getting louder as our impending orgasms finally overtook the both of us together. It hit her first, and I loved the sounds that she made as it washed over her.

"Oh, oh fuck, oh god, yes, yes, oh yeah!"

I felt something hot and sticky splash against my stomach, and as she writhed around underneath me moaning and squealing in pleasure, I knew she had cum. Now, it was my turn. A few more powerful thrusts and I buried myself balls deep inside of her ass and exploded.

I gave a sort of animalistic growl as my whole body shuddered and my cock spewed cum into her rectum. The condom held it all back though, but it still felt just as good to her I could tell.

When I was finished, I pulled out and collapsed at her side, both of us panting as she laid her head on my chest and we stayed there for a few moments. I started trying to register what I had just done.

I had just had sex with a transsexual... a man? No a woman who just happened to have a cock, instead of a pussy... but that was okay with me. At this point, it had to be, hell I had just jerked her off while I was fucking her in the ass.

"So, what did you think," Lisa asked finally.

"That... that was fucking hot," I replied. She laughed and reached down, pulling the condom from my dick and tossing it in a trashcan next to the mattress.

She climbed on top of me and rubbed her gaping asshole against my now flaccid dick again, until I felt myself starting to get hard again. Just when I thought we were going to have another round, she slid down my waist a little and started licking her cum up from my stomach. I only just then realized, she had cum all over me. Not that it bothered me, but it was funny to think.

Once she had licked it all up though, she moved back up and kissed me on my lips, sliding her tongue into my mouth and letting me taste her semen. We parted our kiss and Lisa smiled seductively at me.

"How's it taste? It's all because of you, so I figure you have a right to see what I taste like."

"It's not bad," I chuckled. "There's not much taste really."

"Well, how about next time... you can try sucking me off?"

"Oh... uh... I don't know,"

"Oh, come on," she begged. Lisa now sounded strangely like Rob, as I couldn't help but laugh at that, and so did she.

"It's not like I'm asking you to bend over for me or anything, wouldn't you eat pussy?"

"Yeah... and I have... plenty of times."

"So your basically still orally pleasuring a girl, it's just a little different than it normally would be. Give it some thought, and we'll see what happens."

"Yeah," I replied honestly. "I'll think about it."

We got up and started to dress, and I took note of how patient Lisa really was being with me about everything. She had led me through a very sexual fun adventure, at a steady pace that was comfortable for me. And even though she was requesting a little more from me next time, she was making it clear to me that she would not be angry if I said I didn't want to do that.

Truth be told, I did not know if I wanted to do that or not yet. However, I would definitely put some thought into it, as I had promised her I would.

When I left the club that night with Rob, I told him that he was right. I had a lot of fun, and so far, I had no regrets. I told him about the incident with Kendra and he found it hysterical. That was typical Rob though.

I couldn't wait to come back to The Raven next week.

I hope you all enjoyed this beginning of a new series. I've had this one in mind for a little over a month now and could not wait to write it, but I wanted to finish off Jogging Partners first. As always, thank you to my editor Josie, and look forward to Chapter 2. I'm not sure exactly how long this series will run, but as of right now I have quite a bit in mind for Jay and his adventures.