Jay's Sex Club Adventures Ch. 17

His business partner, who co-owned the construction company he ran was also there. They had been best friends since they were kids, and he took it just as hard as the immediate family had taken his death.

About halfway through the ceremony, I noticed a woman standing off in the far left hand corner of the room leaning against a wall....she seemed rather out of place to be honest. I had no idea who she was, didn't recognize her to save my life. She had shoulder length brown hair, blue eyes, wore a black dress, and her arms were folded over her chest. She appeared to be in maybe her mid to late forties or so. We locked eyes for a brief moment, and then Holly nudged my arm, snapping me out of my trance.

"What's the matter Jay," she asked.

"Nothing I uh..."

I looked back towards the woman, who was no longer paying any attention to me at this point, and shrugged it off. The ceremony came to a close, and the coffin was carried out of the room to the transport that would take it to the cemetary. I was up at the front of the room, standing alongside my mother who was busy greeting family and friends, Holly at my side, when I noticed the woman from earlier walking towards us.

"Are you Stanley's sister," she asked, in a deep husky voice.

My mother turned around and looked at her, an odd expression on her face, as though she too were trying to figure out who this person was. Obviously, I wasn't the only person who had no idea.

"That would be me...and you are?"

"My name is Christina. I was uh...a 'close' friend of your brothers for quite some time."

"Oh...oh," my mother repeated hereslf, as if the first time she had said it she hadn't quite realized what Christina meant.

"I didn't know my brother was seeing anyone."

"We were together a few years. No one really knew except close friends of ours. I just wanted to say how sorry I am that this has happened...in his final days, I tried to convince Stanley to contact you and let you know that he was sick but...he didn't want to worry you. We had a pretty big fight a few days before his death, and we sort of...well, I guess we ended our relationship. I moved out, and wasn't aware of his passing until this past Tuesday."

"I see," my mother said. They continued their conversation for a few moments, and I stood by listening, confused.

I looked over at my father, who was leaning against the wall, paying as close attention as I was. I stepped over to my father and leaned against the wall alongside him.

"What's up dad," I asked.

"Not a thing. Just wondering why the hell Stan never thought to tell anyone he was seeing somebody. Especially someone whose not half bad looking like Christina here...not like he had anything to be ashamed of really."

My dad seemed to be thinking the same exact thing I had on my own mind; why had Uncle Stan kept Christina from all of us?

"I think I know why," Holly whispered alongside of me. I glanced over at her, curiously. "Pay close attention Jay. The tone of her voice, her body, some of her mannerisms...her jaw line."

I looked at all the features that Holly had pointed out to me, trying to put the pieces together and understand what she was getting at here...and then it dawned on me, finally.

"No way...you can't be fucking serious,"

"I am," she laughed. "I guess your not the only one in the family interested in girls like me, are you Jay?"

I couldn't believe it; Christina was a transsexual. It was hard to comprehend, but Holly was right, she definitely did not seem like a typical woman now that I new what signs to look for. It was strange to think that Uncle Stan was into transsexual women...but I almost understood why he had never had kids now, nor had he ever married. Maybe he was more into random hook ups then anything. Still, why hadn't he told anyone?

I doubt anyone in the family would have passed judgment.

"Christina, this is my Son, Jay," my mother said breaking my train of thought. Christina smiled at me and extended her hand to greet me.

"Yeah, I know who you are."

"Uh...you do," I asked, confused.

"You're Uncle talked very highly of you Jay. I saw a few pictures, so I recognized you as soon as I spotted you. He was your biggest fan you know. I heard you inherited the house?"

"Yeah," I replied, calmly. I wasn't really thinking about that at the moment...I was excited to own a house, but I wanted to mourn the loss of a family member, rather than obsessing over that and making myself seem more interested in the fact that he had given me his home on his death bed.

"I have a few things I need to work out with his lawyer, and it's all mine from there."

"That's great; when do you think you'll be moving in?"

"Not sure," I said. "I have some repairs and remodeling I need to do there. Shouldn't take more than a few months or whatever, and after that I'll be settling in there."

"Well, that's good to hear Jay. Here, this is my number," she said, handing me a piece of paper with her cell phone number already scribbled down. "Give me a call sometime, and maybe we can get together and talk about your Uncle. I'd love to get to know the side of him that you knew all these years."

And' with that, Christina turned on her heels and walked away. The days events carried on after that, and I tried not to keep thinking about the fact that I had just found out that my Uncle had been dating a transsexual, and that I apparently had more in common with him then I had thought.

When it was over, we all met up at a local diner for lunch, and after that, I drove back to my parents house to spend a few hours with my mother. Holly of course stayed at my side the entire time, and we hung out there until about 5:00, before we said goodbye to my parents and started making our way back home to our apartment. In the car, Holly could tell I was in a deep train of thought.

"So, I guess you never saw that one coming did you," she asked, catching my attention.

"What...finding out that Uncle Stan liked the same kind of girls that I like? No, I never had a damn clue," I laughed.

"Shame you didn't know...maybe you two would have hung out more often and might not have drifted so far apart."

"Yeah," I chuckled. "Somehow, I don't think I would have liked to discuss my sexual experiences with my Uncle, even if he was into the same things."

"Oh c'mon Jay; you wouldn't have gone to a T-Girl strip club with your Uncle," she joked.

"Shut up," I laughed. She knew I was joking of course. My mind drifted from the shocking revelation about my Uncle, to how I intended to pay Holly back for being such a huge source of support for me this past week.

"You know," I said. "I know you said not to thank you again...but, I really want to pay you back for everything you did for me this week in some way."

"Oh please Jay, don't-"

"No, don't say anything; I have an idea okay?"

I pulled the car over off the road to an area where we were pretty much out of view from the traffic passing by. Then, I stepped out of the car, Holly sitting in the passenger seat confused and trying to figure out what exactly I was doing. I walked around to her side of the car and opened the door for her with a smile.

"Step out of the vehicle please, ma'am."

"Problem officer," she asked jokingly, with a teasing voice.

"I'm going to have to do a random strip search."

"Oh really," she asked, stepping out of the car. "And' what for?"

"Just routine," I replied with a grin. She smirked, and kissed me on the lips, as I gently pushed her back against the car.

My hands began to roam, up and down her sides and along her back. I broke the kiss, and turned her around, leaning her over the hood of the car and feeling her up as if I were trying to make sure she had nothing on her.

"Mm, your awfully touchy for a police officer," she joked.

"Like I said ma'am; just routine procedure."

"Well...I think I like this routine," she chuckled. I moved my hands up her stomach, fondling her breasts, tweaking her nipples with my fingers. Then back down her stomach my hands roamed, over her hips, one hand moving up her leg and under her dress to stroke her stiff cock, while the other moved back up against to one of her breasts.

She sighed, "Jay...stop teasing me."

"Turn around baby," I whispered. I pulled my hands away from her, and Holly quickly turned around, leaning back up against the car for me.

I got down to my knees, lifting the dress up, and pulling her panties aside to reveal her aching cock, dripping with pre-cum. I didn't waste much time, eager to please, I wrapped my lips around her shaft and swallowed her whole. My head moving up and down, my lips sliding back and forth over her cock, Holly moaned and gripped my hair, pulling

lightly.

"That's it baby...fuck...mm, just like that."

I reached behind her, squeezing her ass cheeks as I continued to suck, and pulled her cheeks apart. My finger traced over her hole and I slowly pushed it inside, rubbing her prostate.

Holly tensed up, moaning loudly, and I moved one hand up to her mouth to cover her lips with my finger. I was trying to make sure no one passing by on foot or by car would hear; but she took my finger between her lips and started sucking on it. God, that turned me on even more.

I continued to finger fuck her ass, while her cock started to swell up in my mouth and she began to breathe heavier. Her hips gyrating against me, cock sliding in and out of my throat.

I knew she was at the peak, when she tugged at my hair and shoved herself as deep down my throat as she could, before exploading and unloading her balls down my gullet. I swallowed every drop as usual, licking her clean, and then releasing her cock.

"Mm, wow...that was hot," she whispered.

"We can keep going, if your still horny."

"What kind of question is that," she laughed.

I smirked, turning her around now, still on my knees and now her ass was right up in my face. I spread her cheeks, and she backed up against me, burying my face between them. My tongue licked up and down her crack, tasting her hole, and working my finger back inside of her along with a second one this time around. I now had two fingers, knuckles deep inside of her, massaging her prostate and her cock was quickly growing erect once more.

I started thrusting my fingers in and out harder and faster, and she bit her lip, trying not to scream as she slumped forward against the hood of the car.

I stopped just when I was sure she was about to cum, and stood up behind her, taking hold of her by the hips and probing her hole with my throbbing erection. Holly moaned, pushing her ass back against me, and my cock slipped right into her. Once I was inside, I started thrusting, hard and fast. She slumped against the car hood, shaking the vehicle with every thrust that I delivered, her cock swinging between her legs as I fucked her.

I reached underneath of her, taking hold of her dick and started to stroke it while I continued to plow her ass, nice and hard. I could feel my own orgasm starting to build up now, but I wanted to get her off again before I got myself off.

I started licking and kissing her neck, pushing deeper inside of her, trying to carry her over the edge...and it worked. She cried out in pleasure after a few moments, and I drove myself as deep into her as I could without hurting her.

Her cock spewed cum all over my hand, all over the ground, and her body shuttered between mine and the car. She continued to moan, even after her dick seized to ejaculate, her orgasm still rolling through her despite no longer releasing any fluids. Now it was my turn.

I started thrusting harder and faster again, moaning as I pushed her against the car and my balls began to tighten up, the head of my shaft swelling. I bit my lip, trying not to get to loud, and felt myself let go, firing off several long, thick ropes of hot sticky cum. Holly sighed, as she felt me pumping her ass full of my cum, and when I had filled her to the brink it began to leak out of her hole, and ran down the back of her legs.

I slowly pulled out, and she turned around, facing me on shaking legs and kissed me hard on the lips, tongues twisted together.

"That was great," she said, still out of breath.

"I thought so too. So uh...thanks for being there for me," I smiled. She gave me a light shove, and an evil grin.

"I told you not to thank me again!"

I laughed, pulling her into my arms and kissing her on the lips. What would I do without her, I thought to myself. We cleaned up best we could, put our clothes back on and jumped back into the car, being quick and careful not to have anyone notice. Once we were situated, we drove off, and I felt relieved that we hadn't been caught in the act back there.

At the same time, it had been a lot of fun to do what we had done in such a public area, the idea of being caught had even fueled my arousal...I think it may have even had a similar effect on Holly.

"So...are you going to call your Uncle's ex-girlfriend?"

I shrugged my shoulders; it was a pretty random question. To be honest, I hadn't even really taken much serious thought into contacting Christina, although she had asked me to.

"I don't know...maybe. I'll think about it I suppose."

"You do know she had her eyes on you, right?"

"Oh come on," I laughed.

"No, I'm being serious; she had this look in her eyes. Like she wanted you really bad, ha-ha!"

"Fuck you Holly," I shook my head, laughing nervously.

"Well, you just did a few minutes ago, but we could always go for another round if you feel like pulling over the car again."

Her sarcasm made me laugh more, as I tried to stay focused on driving. When we got home, we immediately went straight to our bedrooms, deciding to take a nap...it had been a pretty long day to say the least. I collapsed onto my mattress, staring up at the ceiling, and my thoughts wandered back to Christina and her relationship with Uncle Stan.

I grabbed my cell phone, and the piece of paper with her number on it, contemplating whether or not this was really such a good idea at all.

Holly might have been right...maybe she did have her eyes on me when we were at the funeral. I had to admit, Christina was pretty attractive. It was a little strange though to think about hooking up with her after she had been with my Uncle. And' honestly, was that really even what she did want?

Before I could make up my mind, my cell phone rang, startling me.

I looked at the screen and it read "Unknown Caller." Curious, I placed the phone to my ear and pressed the talk button.

"Hello?"

"Hi, is this Jay?"

"Yes it is; whose calling?"

"This is Christina. From the funeral."

Holy shit, I thought to myself...she'd beaten me to it.

"Oh...h-hi, how are you?"

"I'm doing good. I just wanted to see how you're doing after all the events that took place today. Like I said, I know your uncle and you were both very close."

"Yeah...I uh...I'm doing alright. Do you mind if I ask how you got my phone number?"

"Oh, I asked your mother right before I left. I gave you mind and completely forgot to ask for yours, and then I couldn't find you after that so I just asked her. I hope you don't mind."

"Not at all," I replied. "Listen...is there anyway we could meet up some place soon and talk? I have some things I want to ask you about my Uncle if that's okay."

"I'd be more than happy to answer your questions Jay; we could do it right now on the phone if you want to."

She definitely did not seem like she had much of anything holding her back. I had to admit, my nerves were through the roof and I knew I could set up a time and place to talk to her, but I really did not want to wait to get this whole thing situated. I decided to take her up on her offer and have the talk right now.

"I hope I don't offend you by asking

this...but...are you a transsexual?"

I'd been rather outright about it; I hoped she didn't get pissed off at me. Better yet, I hoped Holly really was right, because if Christina was actually a real woman she was going to be twice as pissed at me for making such a suggestion.

"Actually...yes, I am. How did you know?"

So there it was. The answer to my question, and Holly really was correct...I knew anyway. She was right with all the features she pointed out, if you looked close enough it wasn't to hard to see.

"I guess, I had more in common with my Uncle then I thought. So it wasn't really that difficult to tell."

"Oh? What do you mean Jay?"

"Well, you saw the girl that was with me earlier at the funeral? She's a transsexual as well. I'm into the same type of woman as my Uncle was into. I never knew he was as well though."

"I see," Christina said. "That's very interesting. Are the two of you...together?"

"No, just...sort of friends with benefits I guess you could say."

"That's nice."

"I wanted to ask you...why didn't my Uncle ever tell anyone in the family about you? And how many other T-girls has he been with, before you I mean."

I got all the answers I was looking for during that conversation. Apparently, Uncle Stan never told anyone about Christina or any of the transsexuals he had dated, because he just never wanted anyone to know...he wasn't ashamed from what she said. He just didn't feel like it was anyones business but his own. From what she explained, Uncle Stan had realized he was attracted to transsexual women in his early twenties, right around the time he got married.

It was actually the reason he and his wife split up in the first place, because he'd had an affair with a transsexual and she had found out about it.

After their divorce was official, he embraced his true self, and never looked back after that.

I noticed Christina seemed to keep flirting with me throughout the entire conversation. I was beginning to feel less awkward about all of this, and found myself openly flirting back. I suppose I thought it would all be innocent, that nothing would come out of it, and if nothing happened then what would it hurt?

Christina told me before we ended our conversation, that she would still like to meet up in person soon even though she had already answered all my questions on the phone; she wanted to get to know me a little better. I agreed and we set up a time and date to hang out and get lunch together. I still at this point, honestly believed, nothing would come out of all of this.

I was going to find out real soon, just how wrong I was. And' my relationship with Christina was going to be more than just sex.