Jay's Sex Club Adventures Ch. 18

A few weeks had passed since the death of my Uncle Stan, including all of the events surrounding it, and my family was still trying to adjust to the loss of such a good person. With spring quickly approaching, I wanted to get out to Jersey, to the house I had inherited from my Uncle, and begin renovations.

I was trying to get myself moved in as soon as possible so that I could enjoy the summer in my very own 'first house'. There were certainly a lot of arrangements that had to be made before I could move in. I needed to get the deed switched over to my name, obtain a New Jersey license, clear out a few personal belongings left behind by my Uncle, and just to top things off, find a new job. Oh, and I still hadn't met with Christina yet to discuss whatever it was she wanted to talk about.

That was going to change today. We had made plans to meet up for lunch after I got out of work, and then we would talk in person and get to know each other a little better as she requested.

After I finished up the last hour of my shift, I clocked out and went upstairs to the store's bathroom to change out of my work uniform, and into some regular clothes. As I left the store and got in my car, I finally had a chance to check her directions. I was driving out to a restaurant in Cherry Hill, New Jersey, which was apparently where Christina lived. She told me we would be meeting at a nice diner that was only a few blocks away from her apartment and a very good place to go for lunch. I told Holly I had plans to meet with Christina today, and would probably be home late after I took care of this.

It was only about half a hour drive from the store where I worked, to this diner in Jersey where Christina wanted to meet. When I arrived, I found myself pulling into the parking lot of a very small diner. Even its lot was tiny, and if the restaurant had been any more crowded than it was, I probably wouldn't have even been able to find an open spot to park.

I shut the car off and got out, shutting the door behind me, my eyes scanning the little parking area for Christina. I quickly spotted her across the lot from me, leaning against her own car, smoking a cigarette. She noticed me before I could start walking towards her, and motioned for me to come over.

"I'm so glad you could make it Jay," she called out.

As I came up to her, I was a bit surprised when she stepped forward and gave me a hug; I had no problem with it. It's just that we hadn't known each other very long and never would have expected such a friendly greeting.

"It's no problem," I replied, pulling back a little.

She smelled great and I suddenly felt myself looking at her in a manner that easily showed my attraction to her.

"Shall we head inside?"

"Sure... follow me," she said with a wink, and a quick twirl.

She seemed to have noticed the look in my eye that said I had been checking her out. She led me up the front steps and through the main doors of the restaurant and requested a table for two.

We followed a busy waitress to the back of the dining area to a small table with two chairs facing one another. She brought us some water glasses, and menus, then left us to make her way over to another table while we thought about our order.

"Please... get whatever you like. Lunch is on me," I said with a smile.

"Oh really?" she asked surprised, then smiled, "Well, you are quite the gentlemen. Much like your Uncle."

Returning her smile, I flipped open my menu and tried to figure out what I wanted to eat. We both ordered something small, though I told her she could have gotten more if she wanted. Two cokes, a salad for me, then I ordered the bacon cheeseburger and she got the regular burger.

After the waitress had taken our orders, she walked away, leaving the two of us trying to get to know one another.

"So Jay, are you excited about owning your own house?"

"Of course," I laughed, "It was really a very generous thing for my Uncle to leave me that place. I pretty much lived there during the summer months while growing up, and I just loved it. Now here I am, in my mid-twenties with a place of my own, and so grateful to finally be able to get out of that tiny apartment."

"That's great. Have you started the remodeling yet?"

"Next week. A friend of mine is going to meet me over there to help figure out everything that needs to be done."

As soon as I had told Rob that I got the house from Uncle Stan, he acted just as excited as I was. He practically jumped when I asked him to help me take care of the renovations. I went to him because he worked in construction and knew quite a bit more about this stuff than I did.

"What do you plan on doing there," she asked.

"Nothing major. Tearing up floor boards and replacing them, replacing doors and locks, windows too maybe. Then probably wind up re-painting everything as well."

"Well, whatever you do... I'm sure Stan would be proud."

I smiled, nodding my head as the waitress came back and gave us our drinks. I took a sip of my Coke, setting it back down on the table and glanced over at her. There was one question that had been on my mind, one that I hadn't been able to ask her during our conversation on the phone a few weeks ago. I was just hoping that it wasn't too personal.

"Christina? Please excuse my asking this if it's too personal... but I was wondering... why did you and my Uncle break up?"

"That's okay," she said, shaking her head, "I suppose... we just drifted apart... that's all. In the beginning, we had a lot in common, and then over time those things sort of changed. Before I knew it, it seemed like we had nothing in common anymore. Well, I suppose there were still a few things, but not as much as I would, or that even he would, have liked."

"Were there hard feelings when you broke up?"

"Not exactly," she answered honestly, "We just didn't care to talk to each other much after the breakup. Now Jay... it's my turn to ask a few questions about you, if you don't mind."

"Sure," I said, not minding at all.

I had asked her a couple of things already that I hadn't really expected her to answer and she had answered both of them. I at least owed her a few answers to some of her questions.

"How long have you been into women like me?"

"Not very long actually. Almost a year now. A friend of mine took me to this club last summer that consists of mostly all transsexual women and men that are interested in them, and uh... I just never looked back after that."

"I see," she laughed, with a look of amusement on her face.

"You like tranny's more then real girls now?"

I shrugged my shoulders, laughing and blushing slightly.

"Maybe just a little. I never had much luck with real girls and uh... I just seem to have better luck with transsexuals. They seem to like me more then real girls too," I laughed.

"Well, anyone would be lucky to have a man like you Jay. Whether they be a genetic woman or a transsexual. You're a very well mannered young man, and quite attractive too."

Now I was definitely blushing. I thanked her, and we carried on our conversation. She went on to ask me a few questions about the Raven, since I had told her I went to the club. I told her how I had made quite a few really good friends since I started going there, and made sure she understood what I meant by 'friends' to which she laughed once she realized what I meant.

I described what the Raven was like. How it had the basement area separated from the actual club area, with rooms specifically for couples that wanted to have sex and didn't want to rush home with each other to get what they wanted. She found that quite interesting, and almost seemed as if she wanted to check the place out herself. She didn't suggest it though.

"So, all those beautiful young women you've met there, and you don't have a relationship with anyone?"

"Well, not at the moment, there was one person I wanted but..."

I trailed off slowly, and sighed. It had been a while since I had even really thought about Lisa, and I suddenly was beating myself up for thinking of her now. It was still a sore spot.

"I know that look," Christina said, "I take it you've had some heart break since you started going to the Raven too huh?"

"Just once," I replied, "Things just didn't go how I thought they would. She wanted a fuck buddy, and I wanted more than that and it just didn't work out in the end."

"I'm sorry to hear that. What about you and Holly?"

I smiled at the mention of Holly.

"Well, we're not together. We're just..."

"Fuck buddies?"

We both laughed, and I nodded my head, agreeing. Then again, as I thought about it... Holly and I did have quite a lot of sex together, and we were also really good friends, but it didn't feel like a typical "friends with benefits" relationship. We cared for each other. Of course, friends care for each other, but we were always together and always looking out for one another. Maybe I need to take a closer look at what the two of us had?

I shrugged that thought off, fearful of what might happen if I tried to cross the line with Holly.

The line between friends who have sex, and friends who fall in love was a dangerous one to cross. I had already figured that out thanks to Lisa, and I didn't want to ruin another close friendship by making the same mistake. Nor did I want my heart smashed again so soon.

"Jay, I hope THIS isn't too personal?" Christina asked.

She sounded like me now, even had the nervous look that told me she didn't want to offend me by asking whatever was on her mind.

"When it comes to sex, um... do you do all the work, or..."

She left the question hanging in the air, trailing off and waiting for me to answer. I got the hint after a few seconds and chuckled, blushing slightly.

"You mean, whose top and whose bottom?"

"Sorry," she giggled, "Didn't mean to..."

"No, it's okay," I said, "I'm actually pretty versatile."

"Really now? That's quite a rare, but valuable trait to have Jay."

"Yeah, it's hard for me to just settle for one role when it comes to sex. Sex is sex, and it all feels really good."

"Well, I have to say... I wish your Uncle were a little more open minded like that. Hell, we may have stayed together a lot longer if he had been. Stanley was pretty closed minded though."

I just laughed, hoping she wouldn't go too much further... as I didn't really want to know the details of her sex life with my Uncle. Unfortunately though, she did continue...

"I'll tell you, getting that man to even touch me down there was damn near impossible. No touching, no oral... especially no talk about me sticking anything where the 'sun don't shine'. I was the submissive one all the way, with no room for even talking about switching it up. It's a shame too, because I've got a lot to offer."

I tried not to laugh, not wanting to insult her. But it was hard not to laugh when she was spilling all this information about my Uncle. It wasn't much of a surprise to me really though. Uncle Stan was a big guy who looked like he'd climbed down from the mountains. He definitely didn't look like the kind of guy who would be willing to do any of the things that I had done with some of the girls I knew from the Raven.

Suddenly my train of thought was broken when Christina reached under the table and started rubbing my leg. I locked eyes with her, frozen and not sure what to say or do as she ran her hand up and down my leg.

"Do you know what I have to offer Jay," she whispered.

"Uh... n-no," I stammered.

"Nine... hard... thick... inches. Nine inches that are just begging for attention. It's just a damn shame for a gift like that to go to waste... don't you think Jay?"

I was sweating. My heart was racing, and her hand was moving further up my leg towards my crotch, and I was getting more and more tense. Not in a bad way and probably in the exact way that she was most likely hoping that I would feel.

"Ever since I broke up with your Uncle, I haven't been able to find a man willing to switch roles. Didn't use to be that way of course. Back in my twenties, I had a few guys who were more than willing to drop to their knees for me. God it's been so many years Jay."

Finally, her hand reached its final destination and my knee jerked, banging against the underside of the table. She laughed at my reaction and pulled her hand away.

"You alright love?"

"Uh... y-yeah... "

Our food arrived then, and the remainder of our meal was silent as we sat and ate quickly. When we were finished, it was still silent. My cock was still throbbing in my pants and I was still sweating... this was insane. I find out that my deceased Uncle was into transsexuals, much like me, and now I find out that his transsexual ex-girlfriend who use to be a Dom in bed is interested in making ME her first bottom since god knows how long. Did I really have it in me to hook up with my Uncle's ex-girlfriend though?

"Are you okay Jay? You haven't spoken since before our lunch arrived."

"Yeah, I'm fine. Just... thinking."

"Well, so am I... I'm thinking about you. And what I would love to do to you. I'm thinking about the dirty... nasty... things I would love to do to you once I get you back to my apartment."

I couldn't take it anymore. I realized now that Holly had been right, Christina was definitely trying to get in my pants... and she was going to get what she wanted. I didn't think Holly was going to care much, she would probably make a joke out of it. She'd made a joke out of the whole idea of Christina wanting me in general.

"Check please!"

The waitress had been watching us from only a couple tables away, and smiled at us both as she totaled our bill quickly and wished us a 'VERY good afternoon'. I glanced over at Christina, and she smirked at me. I paid the bill, and we practically left the restaurant together at a full run.

Christina told me to follow her in my car, so I wouldn't have to leave mine behind at the diner. On the way to her apartment I started thinking more about what I was getting ready to do with her. This was still insane, but I wasn't thinking entirely with the head on my shoulders... it was more like half of that head, and half of my other head... if you know what I mean.

It wasn't the age gap that was awkward, she was in her mid to late forties, but I kind of liked older women anyway. If there was anything about this bothering me, it was that I didn't know what my Uncle would think if he knew I was hooking up with his ex. I shrugged it off, assuming he would probably make fun of me or something. Lost in thought, I almost failed to notice she made a hard left turn, but I managed to make the turn and stay on her tail. She made another left turn a few blocks down into the large parking lot of an apartment complex.

I parked my car right next to hers, shut off the engine, and got out as she closed her door and switched on its alarm. She smiled at me, stuffing her keys in her purse and stepping close.

"Glad you were able to stay behind me... come on!"

She took me by the hand and led me to the entrance of the complex. Behind the doors there was a massive lobby with marble floors, and it appeared to be a well kept and fancy complex. We stopped at the elevators, and she pressed the up button. The door slid opened, and we stepped into the elevator car, watching as the door slowly closed behind us. We were the only two onboard and as I looked over at her... she was once again giving me that wicked smile, before pushing me back against the wall and pushing her floor button.

The twelfth floor... we had to go up twelve floors!

Pinned against the wall of the elevator, I groaned as Christina's lips collided with my own and her tongue slipped past my lips. Her hands and lips were now all over me, roaming every inch of my body, kissing, licking and sucking at my neck. I couldn't believe it, but we made all twelve floors without a stop and remained the only two on the elevator the entire time.

When the doors slid open, she pulled me through them and led me down a hallway towards the door of her apartment. She let go of my hand long enough to pull the keys from her purse again, and unlock the door, before dragging me inside and shutting it behind us. Then, once again I was pushed up against a wall. But this time she was taking it further then just passionately kissing me all over. She dropped to her knees and unfastened my belt and pants, pulling them down around my ankles, and swallowed my entire cock... in one move.

"Holy shit," I whispered.

She was a great cocksucker... Uncle Stan had been one lucky guy that was for sure. She could deep throat like an expert, and the only other person I could think of that was that skillful was probably Holly. Her hands slipped up under my shirt, pinching my nipples as she held my cock deep in her throat, massaging it with her muscles.

Then she released me and stood up,

crushing my lips with her own once more.

We made out passionately, tearing the clothes from our bodies as we gradually made our way towards her bedroom. Once we reached the mattress, I was completely stripped and she was down to nothing but her panties, which did nothing to hide the massive bulge that she had tucked away between her legs. She stepped back to the middle of the bedroom, and slowly slipped her panties down her legs, tossing them aside.

She parted her legs, and her cock sprang free, standing at full attention, and my eyes went wide with lust. I had been with girls that big before, there was Kendra and Christy. It wasn't shock in my eyes, it was pure lust. She had me right where she wanted me.

"You're turn babe," she said, in a seductive voice. I stepped forward and knelt down in front of her, her cock right up in my face.

She smelled clean. I licked the tip and started licking up and down the length of her shaft. I then swallowed her whole, taking as much of her big cock as I could manage down my throat. She gasped, pulling at my hair and leaning her head back in surprise.

"Oh my! Oh Jay! You're... you are REALLY good at this!"

I gave no reply, staying focused and trying to please her to the best of my ability. Up and down I bobbed my head, my lips sliding back and forth over her cock, gagging, slurping. I reached up to play with her tits, gently rubbing and pinching the nipples, and then moved one hand back to her ass and gave it a nice squeeze.

"Oh wow," she moaned, "Oh please... you have to stop!"

I did as she had requested, pulling her cock from my mouth, making a wet popping sound and looked up at her.

"Everything okay?"

"Oh, it's more then okay. But if you keep going like that, I'm gonna cum any minute now. We want to save the big bang for the main event, don't we baby?"

I knew what she meant. She wanted a piece of my ass, and I was definitely willing to give her what she wanted. Christina instructed me to get on the bed, and to lift my legs up as high as I possibly could. I followed her demands, pulling my knees up to my chest, and she climbed onto the mattress with me and grabbed a bottle of lube.

She applied plenty to my waiting ass, and smeared an extra bit to her throbbing erection before pressing the tip to my entrance. I took a deep breath now and held it in. I was no beginner, and it often helped with the first thrusts when it came to bigger girls like Christina.

Christina thrust forward, plunging balls deep into my tight asshole. I blew out the breath of air, and groaned, my asshole spreading wide open around her huge cock. She was so deep inside of me, and already right on that spot that I loved. She pulled about halfway out and thrust right back into me, and wasting no time she began pounding my ass with long hard strokes.

The bed shook underneath of us, and the sound of our bodies slapping together echoed through the room.