tagTranssexuals & CrossdressersJay's Sex Club Adventures Ch. 13

Jay's Sex Club Adventures Ch. 13

byWhiskeyIsGood©

Three weeks had passed since the New Year's party... three weeks since Lisa left Philadelphia, without so much as a goodbye. Just a simple note, trying to explain herself to Holly and I, but not really making as much sense as she probably had hoped to make. What did she expect though... for us to be okay with the fact that she would just take off like that? Especially me, knowing how I felt about her, or at least she claimed that she knew. Yet, it was so easy for her to just pack up and take off, like it was nothing.

I hadn't been out of my room, let alone the apartment, very often since the day she left. I would leave three times a day, once to go to work, once to get dinner and whenever I had to go to the bathroom. Other than that, I had been confined to my room, not really wanting much of anything to do with the outside world. I hadn't even bothered with the internet, it had been days since my last Facebook account update.

Missed phone calls and text messages were starting to gather on my cell phone, and I barely even noticed when my phone would ring. Most of the calls were from Rob, a few were from Annie and Jen. They were all worried about me, Holly most of all probably.

Holly wasn't acting much differently. We saw each other when passing in the apartment, but did not talk very much or do anything. I don't think either of us had sex with each other, or anybody else for that matter, in quite a while.

I sighed to myself... truth be told, I was more worried about Holly than I was about myself. Little did I know, my isolation and depression were about to come to an end in a few short minutes.

Leave it to Rob to make damn sure of that!

I had managed to roll out of bed on one of my days off from work, and decided to spend yet another lazy day lounging on the couch instead of staying confined to my bedroom all day. I cracked open a beer, laid down on the sofa, and clicked on the television. I was flicking through channels trying to find something worth watching, when I heard a loud knock at the apartment door.

Startled, I jumped, spilling a little bit of beer on my shirt. I sighed, irritated and glanced at the door hoping whoever it was would just go away. A few moments of silence, and then again, they banged on the door. I stayed silent, muted the TV, and leaned my head back and groaned. Just when I was starting to think whoever it was had given up, they again started pounding on the door, and this time shouting my name as well.

"Jay... I know you're in there. C'mon dude, open up!"

I knew the voice. Rob must have gotten tired of me ignoring all the phone calls and text messages. There were probably a few on my Facebook as well. Again, he shouted through the door, calling my name and I decided that I was going to have to answer, I knew he wouldn't leave until I did.

"Hold on," I yelled back, standing up and walking across the living room to the apartment door.

I unchained and unbolted the locks, pulling the door open and there stood my best friend with a concerned look in his eyes.

"Dude... you look like shit."

"Nice to see you too," I said, turning away and walking back into the apartment, but leaving the door open so he could follow.

"What's going on Jay? I haven't heard anything from you in days man. Holly too, we've been going nuts trying to find out if you two are alright and we can't reach-"

"Maybe, we don't want to be reached."

My voice was harsh, and Rob fell silent. I immediately felt bad for snapping at him. I sighed, turned around and leaned against the back of the sofa, staring at him.

"I'm sorry," I said, as my head fell and voice cracked, "I just... there's nothing I can say really. I'm not okay, but that's not what you want to hear."

Rob shut the door and we both dropped down onto the couch, silence hanging in the air for what felt like an eternity. Finally, he sat forward, running a hand through his hair and glanced over at me.

"You really loved her didn't you? She really messed you up."

"Hah... yeah, well... you know what they say, 'love hurts' right?"

He nodded his head, and gave me a pat on the back.

"Look, why don't you come out with me tonight? I'm heading over to The Raven, and there are a lot of people who would love to see you."

"Rob... I don't know..."

"It's not a suggestion, your coming with me."

I laughed, and he gave me a playful shove, standing up in front of me and folding his arms over his chest. I looked up at him and sighed, knowing that he was totally serious. He would drag me out of the apartment absolutely kicking and screaming if he had to... Rob was a good friend like that.

"Fine," I said finally. "Give me twenty minutes."

I stood, started walking down the hall to my bedroom, when he called after me, "Where's Holly?"

"Work... won't be home until after midnight."

"Shame... would've been nice to bring her along too."

He was right, I thought, as I stepped into my bedroom and shut the door behind me. I suddenly deeply wished that Holly were here right now so that she could go with us too. She was just as messed up over Lisa as I was, but for different reasons. Where I had been in love with Lisa, Holly had viewed her as her best friend. It was a broken heart either way though, whether they were in love or best friends, we each knew how the other felt.

I decided that this weekend I was going to do for Holly what Rob was currently trying to do for me. I was going to drag her out of the apartment and attempt to help her get out of her depression. Hell, maybe we could even help each other get out of it...

I started getting ready, taking off my shirt and entering the bathroom. A quick shave, and then I hopped into the shower to wash up, before putting on some fresh clothes and grabbing my Flyers hat.

Leaving my bedroom, I glanced at Lisa's door, realizing I had been avoiding it for weeks, then walked back down the hall and met Rob in the living room, right where I had left him.

"Ready to go?"

"As I'll ever be."

And out the door we went. The Raven wasn't very far, and figuring I would probably have a few drinks tonight, we decided to just leave our cars here, and walk to the club.

As we arrived, there was the familiar sound of loud club music pumping through the stereo system. We walked through the door and looked around, taking in our surroundings. It had been no more than three weeks, but it felt so much longer since the last time I came here. Rob and I walked straight towards the bar, pushing through the crowd as we walked and finally we took a seat side by side.

Rob bought me a drink and I leaned back and relaxed for what felt like the first time in a long time, enjoying the feeling that came with being out of the apartment for something other than work.

"Look at this," Rob said, motioning towards the dance floor, "so many beautiful women, huh? My God, look what you've been missing Jay!"

He was right... I laughed, but he was totally right. There were a lot of beautiful girls here tonight, and already I was starting to feel aroused from the mix of alcohol and the scenery. My eye caught the curtain that blocked out the DJ area, and my mind immediately went back to the Christmas Eve Party.

Lisa and I behind the curtain, having some of the best sex we ever had together while she was supposed to be controlling the music.

It was a good, and yet depressing memory, and I had to quickly push it out of my mind taking a swig from my beer and sighing.

"You alright bro?"

"Yeah," my voice again cracking, "yeah I'm good."

"Well, look who finally came out of his cave!"

As I turned around on the bar stool, I swung right into the open arms of Jen, who laughed as she embraced me. I chuckled, wrapping my arms around her and pulling her close, inhaling the scent of perfume as we hugged.

"Where the hell have you been," she asked.

"Uh, well you know... around. Just um... Working and stuff."

"Yeah, I'll bet," she said sarcastically, then sighed as she continued, "I heard what happened with Lisa."

"Eh, it's no big..."

"Don't say it," she cut me off holding a finger to my lips, "It was a fucking big deal, Jay. What she did was way fucked up, and you know it. She screwed you and Holly both, and not in a good way."

Strangely enough, while I agreed, I didn't want anyone to be angry with Lisa. I knew what she had done was wrong and yet I still had the urge to stick up for her. But this wasn't the time for that, because Jen meant no harm and to "stand up" for Lisa would only make me seem like a jerk towards a good friend with good intentions.

"I'll be alright Jen," I assured her, "Really... life goes on, right?"

She nodded her head, and with a very feminine motion, wiped a strand of hair out of her face, curling it in back of her ear and kissing me on the forehead.

"I have to go, but we should get together soon... Holly too, deal?"

I smiled and we shook on it, hugging one more time as we exchanged a kiss and then off she went to make her way home. I turned and looked at Rob, who flashed me a smile, and I rolled my eyes and laughed.

"I have to take a piss," I said walking away from the bar towards the rest room area.

I walked into the restroom and approached one of the urinals, unzipping and emptying my bladder. As I stood there, I could hear the passionate moans of two people in one of the stalls having what sounded like some pretty intense sex. I laughed silently to myself, flushed the toilet, zipped up and washed my hands before leaving the bathroom. As I walked out of the restroom, I was met by another familiar face, this time it was Kendra.

"Well, there he is," she exclaimed, "I haven't seen you in ages!"

We hugged, and exchanged a kiss before she gave me a slap on the ass. Her smack was still just as strong as ever and I felt the sting even a minute later.

"Where has my sexy little bitch been lately?"

"I um... I've had some stuff going on, that's all. But I'll be around more often now, I'm looking to get back in the game so to speak."

"Oh is that so? Well... maybe we should spend a weekend together soon, how does that sound? Just you and me, alone in my suite. Mm, I can think of so many things I would love to do to you baby."

Suddenly I could think of a LOT of stuff I would love to have her do to me and the thought of it all gave my cock a twitch and I gave it a cursory rub through the fabric of my pants. She must have noticed, because she grinned evilly at me, before pushing me back against the wall behind me and crushing her lips against mine. I felt her wet tongue slither past my lips, and her hand pushed mine away, groping my cock through my pants.

At her touch, I felt myself getting harder and harder. She broke the kiss, and starting kissing and biting at my neck, earning a low moan from me as she ground herself up against me.

"Of course... we could always have some fun now, if you want."

That was a suggestion that I did not think I could say no to, and I responded by kissing her on the lips once again and pulling her into the bathroom behind me. The couple that had been going at it seconds before had left their stall and were walking out just as we were barging in.

Kendra resumed control, my sudden burst of dominance wearing off quickly, and she pushed me into one of the stalls and stepped in closing the door and locking it behind her.

"Maybe just a blowjob," I said. "I haven't uh... been fucked in a few weeks. So I'm a little out of practice."

"Well that's no way to 'get you back in the game' baby. But... maybe a blowjob will do me for right now. Then we can really get back in the game this weekend."

She winked at me and I smiled as she started kissing my neck again, pushing up against me and I could feel her throbbing erection pressing at my thigh.

She stopped her assault on my neck, and I quickly dropped to my knees, lifting her skirt and pulling her panties aside. Kendra's massive cock flopped out, already as hard as a rock. I licked my lips and began kissing the tip, while teasing it with my tongue. Kendra sighed, running her hands through my hair as I continued teasing her with my tongue and cradling her balls.

Finally, when I felt like I had spent enough time torturing her, I ran my tongue up and down the length of her shaft before engulfing her, all the way to the back of my throat. I gagged a little, the familiar slurping sounds escaping my mouth as I started to deep throat.

I was bobbing my head up and down, savoring the taste of her cock, while breathing in the musky aroma of her balls. It wasn't long before Kendra was moaning louder, pulling my hair and forcing herself as deep down my throat as she could manage.

My body was shaking, then I choked, as my gag reflex kicked in once more, and Kendra cried out in pleasure, stomping her high heeled right foot again and again. Now her cock swelled even larger, cum bursting from the tip and shooting down my gullet.

As usual, I swallowed every drop, licking her clean and then stood up and kissed her on the lips. She smiled, still a little out of breath and reached behind me to give my ass a squeeze.

"Still as good at sucking dick as I remember baby... I'm impressed."

"I try," I smiled back.

"I know... I would really love a piece of that ass right now. But we can wait until you're up for that again. You open this weekend?"

I thought about it for a moment, and was about to say yes, but then I remembered my intentions to try and break Holly out of her depression. I would have loved to spend a couple of days with Kendra, don't get me wrong now... but Holly was at the top of my priority list for the moment.

"I have something I have to do this weekend. But I'm all yours the following weekend, if you think you can wait that long?"

She caught the hinting tone in my voice, and the seductive grin on my face and she giggled, giving me a peck on the lips.

"I can wait," she was trying not to sound disappointed, "you're lucky I'm such a nice girl."

"No... I'm VERY lucky," I laughed.

We cleaned up, before heading out of the restroom and going our separate ways. Kendra said she had to get home since she had to work the next day, so she left right after our little encounter came to an end. I made my way back towards the bar, where I found Rob sitting where I left him, on his third beer.

"Did I just see you come out of the bathroom with Kendra," Rob asked.

"Maybe... what if you did?"

"Hah, hah, some things never change, do they Jay?"

I laughed, giving him a shove and sitting back down at the bar. I washed away the taste of Kendra's cock with a fresh cold beer, as Rob and I resumed our conversation from earlier. It was getting late, and I had decided I was going to head home, giving Rob a hug and thanking him for prying me out of my depression for the night.

Just as I was about to leave though, I caught sight of another friend... Claudia.

Rob had already walked out the front door, but I wasn't one to leave without saying hello to a friend, that would be rude.

I walked over to Claudia, taking her by surprise and she seemed just as excited to see me as Jen and Kendra had been. We hugged and kissed, and walked over to the bar where I bought her a drink, sitting down to talk. One thing that differed between talking with Claudia and talking to Kendra or Jen, was that Claudia did not bring Lisa up to me at all.

She probably knew what happened, I was sure, but it was nice not to have to talk about the thing I had come here to get away from thinking about. The night wore on and soon it was closing time, The Raven started emptying out and Claudia and I followed the crowd outside into the cold night air.

"So," she said, scuffing the toes of her high-heeled shoes on the ground while biting her lower lip. "Um... you heading home now... or maybe you would like to come home with me ... um, maybe have a little fun?"

I had already done some stuff with Kendra; but it wasn't unlike me to hook up with more than one girl on the same night at The Raven. That was how I had always been before, leading up to when I stopped going out from my depression, now I didn't want to go home.

"I think I'll take door number two," I laughed.

"Good... let's go then," she said, grabbing me by the hand and pulling me down the street behind her.

We laughed and talked as we made our way back to Claudia's apartment, and when we got there and entered the room, she wasted no time pinning me against the wall and crushing her lips against mine.

I was kissing her deeply and moaning, then suddenly she was fumbling with my belt. I sighed, as she slid down to her knees and yanked my pants and boxers down, my cock standing at full attention instantly. She innocently smiled up at me, before giving the tip a lick and then swallowing me whole. I moaned softly, as Claudia began sucking and stroking, playing with my balls while she sucked.

I had always considered her to be one of the best when it came to performing oral sex and my opinion had not changed since our last encounter.

Moving from the living room to her bedroom, we tore off the remainder of our clothing on our way there.

She threw me onto the mattress, and I laughed as it bounced beneath me, then she jumped on beside me. We went right back to making out once again, as she stroked my cock. She sat on top of me and grabbed her cock along with mine, stroking them against one another. She leaned in close, kissing my neck, and working her way down, to lick and suck on my nipples. I could feel a rush of pre-cum leaking from the tip of my penis, as she continued stroking.

In my favorite position, I leaned up and swallowed her cock as she went down on mine. The both of us sucking each other, I started working my index finger into her hot tight asshole while I went to town on her dick.

Claudia moaned against my cock, the vibrations sending pleasure up and down its length. I felt my body tense up as I was going to cum, but I did not want to cross that line just yet,

"S-Stop!"

"What's the matter," she asked, releasing my cock from her mouth with a wet popping sound.

"Nothing... it's great, I just don't want to cum yet."

"Oh, I see," she said seductively turning around to kiss me again. "I would much rather you blow that big, hot load in my ass anyway. What do you think?"

"I think, I've never heard a better suggestion."

Her eyes filled with lust as Claudia reached behind to take a firm hold of my dick, guiding it between her big ass cheeks and into her tight hole. I moaned as I felt her tightness wrap around my shaft, the first time I had actually fucked anyone in three weeks.

I grabbed hold of her hips almost immediately, once she had lowered herself all the way down onto me, and started fucking her like crazy. She was bouncing up and down, her ass cheeks slapping against my hips, her cock flopping about. I grabbed on to it and started stroking her while I fucked her and she started moaning louder.

Her sounds of pleasure fueled my own pleasure, and I pulled her towards me to kiss her once again. Both of us out of breath, I started thrusting upwards into her, harder and faster, as I felt the beginning of my orgasm starting to build.

Claudia obviously felt it coming on too, because she started squeezing her ass around my cock, tightening her grip on me so she could push me over the edge. It worked too, because a few moments later, I arched my back and cried out, as my balls started pumping a massive, thick hot load deep into her asshole. Claudia moaned and groaned, grinding against me as she felt my dick pulsating deep inside of her, filling her with my semen.

I felt my senses beginning to return, as the orgasm subsided slowly but surely. When it was over, I realized she had yet to get off herself... that was not okay with me. Tired as I was, I wanted to make sure that BOTH of us got off tonight, not just one or the other. So I pushed her off of me, taking her by surprise for a moment and shoved her onto her back. I started kissing my way down her stomach, towards her groin, and she immediately got what I was about to do.

Report Story

byWhiskeyIsGood© 6 comments/ 25491 views/ 34 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel