tagTranssexuals & CrossdressersJay's Sex Club Adventures Ch. 08

Jay's Sex Club Adventures Ch. 08


A little later that evening at Rob's party, after our very serious conversation, Lisa and I finished my bottle of Jack Daniels together. And by this time, we were both pretty fucking drunk... Rob was already inside, passed out on the couch.

Hell, just about everyone here was either drunk, or if they had brought weed, were stoned. I wandered into the house, heading for the bathroom to relieve my bladder. My stomach churned a little as I walked towards the restroom, and for a moment I worried that I may end up puking. I started walking faster, throwing open the bathroom door, dropping to my knees in front of the toilet, but... nothing.

Thank god for that much. After a few moments, when I was sure that nothing was going to come up, I got back to my feet and sighed in relief. I lifted the toilet seat, pulled out my dick and started to relieve my bladder. When I finished, I thought maybe I needed some water... hopefully, that would help relieve some of my nausea.

I realized it had been two years since the last time I drank as much Jack Daniels as this, so I figured it was best to try and sober up before I got sick.

I went downstairs to the kitchen, and found a clean glass before pouring myself a glass of water, I took a long swig and sighed. It tasted like heaven going down, and I quickly emptied the rest. Turning the sink on again, I started refilling the glass, and as I did, I heard footsteps behind me.

"You okay there," came an unfamiliar voice.

I turned around, to find myself looking at a tall woman, maybe in her early thirties with sandy blonde hair and green eyes. She had an incredible body, and was wearing a tank top that showed a nice view of her tits. She also wore a white skirt, showing off her sexy smooth legs.

"Uh... y-yeah, just needed to sober up some," I slurred.

"You look pretty drunk. are you sure you don't need a hand?"

"No, no I... just wanted some water."

She leaned against the kitchen counter, as did I, and her kind smile turned a bit more seductive.

"You must be Jay," she said, "I've heard a lot about you... like how you're really good at sucking cock."

"Oh... who told you that?"

"Kendra," she said, to my surprise, "She's a good friend of mine."

That was great, I now wondered if this girl had a dick as big as Kendra's. Maybe that was why Kendra suggested me to her.

"Listen... if you feel good enough later... meet me upstairs in the guest bedroom. We can have plenty of fun together, I'm sure."

I took another swig from my glass nervously, and the girl laughed, helping me into the living room. I sat down on the couch across from where Rob was sound asleep. Making myself comfortable, I looked at her... the room was spinning, and so was she.

Groaning loudly, I sat the glass down on the floor and lay back on the couch. She smiled down at me.

"Thanks," I muttered, sleepily. She faded out, as did the sounds that I could hear coming from out in the backyard... I had passed out.

When I woke sometime later, I again groaned, pushing myself up into a sitting position. My stomach churned, and I leaped off the couch making a dash for the bathroom... but this time, there was no holding back the contents of my stomach. Half a bottle of Jack had done me in. Back in the day I could have handled it, but it had been too long since I'd been drinking this heavily.

When I finished, I sat on the floor next to the toilet, totally exhausted.

I didn't really want to get up for fear of not being able to make it back to the bathroom again if I had to. The doorknob turned, but it was locked.

"Whose there," I yelled.

"Jay, is that you?" a very concerned Holly asked,

"It's me, are you alright?"

Grunting, I pushed myself onto my knees and unlocked the bathroom door, pulling the door open and letting her in.

"Holy shit! Baby... you look like hell."

"I feel like hell," I laughed. Holly didn't appear that drunk to my surprise, as she started laughing and shut the door behind her, and sitting down on the floor with me.

"To much Jack," I groaned. "Where... oh boy... where's Lisa?"

"Passed out on the couch. I just helped get her comfortable."

"At least one of us is sleeping," I said.

"Well, when you're sure your okay, I'll help you get up to the guest room," she offered.

I smiled and nodded my head as she started rubbing my back. It was good to have someone at my side, trying to comfort me... I hated being sick while drinking. It was the only reason I hated drinking that heavily.

"Hey Holly... who was the girl with the Sandy blonde hair and the white skirt and tank top?"

"Oh... are you talking about Christy?"

"I guess so. She ran into me in the kitchen and I think she made a pass at me."

Holly started laughing, and I chuckled, weakly. I leaned my head back against the wall and cleared my throat, continuing to explain.

"She told me to meet her in the guest room if I was interested. Said she was friends with Kendra, and that she heard a lot about me."

"Well, you are way too drunk for that right now. I won't let you go hooking up with anyone if you're this messed up Jay. If you want to hook up with Christy, you can do it when you're sober."

"Should I though? I mean, what do you know about her?"

"She's pretty nice. She's got a big cock," she laughed, "Not as big as Kendra though from what I hear, but she damn sure knows how to use it."

"Oh yeah? What's that mean?"

"I don't know," Holly shrugged her shoulders, "I hear she has this special trick that she's able to do while she's fucking a guy in the ass... they say she's really flexible, and since she's pretty big, she can actually fuck you in the ass in missionary, and suck your cock at the same time."

"No fucking way," I blurted out. We both started laughing, and I shook my head, trying to take in what she had just told me about this girl. If it was true though... damn! It had to take some serious talent to do that. It sounded hot too, and I could just imagine taking a good pounding, while getting my cock sucked by the same person giving me the pounding.

"I think I'll give her a try," I said.

"Fine honey... but not tonight. Like I said-"

"Yeah, yeah... I know! I'm too drunk. What would I do without you?"

"I'm not sure," Holly laughed, "but you're lucky to have someone like me watching over you. You and Lisa both for that matter!"

When I felt like I was good to go, Holly helped me get back up on my feet and then helped me up the stairs to the guest bedroom. Christy wasn't in there, which was no big deal. I would get her number from someone in the morning if she wasn't still at the party by the time I woke up.

I flopped down on the mattress, and started laughing as I pulled my shirt off and tossed it to the floor. I kicked off my shoes, and Holly helped me get out of my pants. Once I was stripped down to my boxers, I collapsed face first into the pillow and groaned, as the room started spinning once again.

"Thanks Holly," I mumbled.

"No problem Jay. Now it's my turn to get some rest."

I heard the door click shut behind me, and I sighed as my body began to relax. I was ready for sleep, but the only problem was, this room was so damn hot I couldn't take it. Figuring no one would care, even if they walked in and saw me, I slipped out of my boxers and proceeded to bury my face in the pillow once again.

Sleep overcame me quickly, as the cool night breeze swept over my nude body.

I woke again about midway through the night. I wasn't sure what time it was. I just knew that I had been woken up by the presence of someone else in the room with me. I had even heard the door opening and closing. Shivering, I stayed totally still and tried to get back to sleep. I assumed it was probably Lisa or Holly, and figured it would be nice if we would sleep in the same bed anyway.

"I knew I would find you in here sexy,"

The voice did not belong to Lisa or Holly; I did vaguely recognize it though, and I knew who it was... it was Christy. Holly had insisted I was too drunk to have sex with anyone, but Christy was here right now, I was naked and also a bit horny... as well as very curious about whether what she told me about Christy was true.

I heard the soft patting of her feet on the carpet coming towards the bed. I felt the edge of the mattress pushing down, as her weight moved over top of me. I remained flat on my stomach, face against pillow, as Christy crawled over me. The warmth of her body felt good, and I sighed as she relieved the chill that had been running up my spine.

Then I felt something big and hard rubbing against my ass crack, and I knew just what it was... damn, she did feel pretty big. Suddenly, Christy turned me onto my back and smiled at me before kissing me on the lips. I embraced her, kissing back, our tongues locking together.

After a few seconds of kissing, she started teasing my nipples with her tongue while reaching down to take hold of my dick and stroke it for me. Up and down her hand glided over my dick, while her tongue continued licking at my nipples, and she began to suck on them as well.

"I want to suck your cock baby," she whispered.

She slid down some and wrapped her lips around my dick. It felt so wet, and warm, but even though the booze was wearing off, I noticed there was a bit of a problem... as good as all of this felt, I couldn't seem to get hard. She had made out with me, played with my nipples, and was now straight up sucking my cock... and I still couldn't get a hard-on.

What the hell was going on, I wondered. Then it dawned on me... I was sobering up, but I obviously still had a bad case of whiskey dick as I liked to call it during my college days. Christy stopped sucking, and looked up at me a bit confused and I leaned my head back in shame and embarrassment. I worried that she might be angry with me or something, and I hoped I was wrong.

"I'm sorry... this isn't normal for me, I swear."

"What's the matter?" she asked a little confused.

"I... I think I drank too much. I got whiskey dick," I laughed.

"That's it?" Christy asked.

I gave an uncertain look and then she laughed as well, kissing me on the lips.

"I was worried I was doing something wrong or that you weren't attracted to me or something. If it's just because you're drunk, that makes me feel a lot better... there are other ways to please the both of us."

I laughed, certain I knew what she meant by that but not so sure I wanted to take that step... after all, she was supposedly as big as Kendra. Holly said they weren't the exact same size though, so maybe it wouldn't be so bad and I definitely was very curious about her 'trick'.

"So Jay... if you can't get it up, that's okay. Because I can get it way up, so we can just... reverse the roles a little, if you don't mind."

"Not at all," I replied.

"Good," she said, as she stood up on the mattress and slowly slid her skirt down her smooth legs.

I was surprised to see that this whole time she had not even been wearing any panties under that skirt. So as soon as she pulled the skirt off, her cock sprang free immediately, fully erect and huge.

Holly was right. Christy was definitely very large. Still not as big as Kendra though, which was good in my opinion, because it meant I stood a better chance of experiencing less pain when it was over.

Christy stood over me, with her feet planted on the mattress on either side of my head, her huge cock dangling right above me. Smirking down at me, she started to lower herself down until her cock and balls were right over my face. I opened my mouth as her balls slipped in, and I started sucking on them both, one at a time. Christy moaned, leaning her head back as I sucked on her nuts, and she started stroking her cock.

After a few moments, she let go of her cock and pushed that between my lips. It took a few seconds for me to accommodate her size, and once I had adjusted, she slid all the way to the back of my throat with ease. It wasn't fitting her entire length in my mouth that worried me... it was fitting it all in my ass that I was unsure of.

It had been a while since I last took a pounding; since my experience with Kendra to be exact. So I was certain it would probably be extra tight for her back there. With her eight-inch monster deep down my throat, I gagged, loving it, and sucked her to the point where I knew she was enjoying herself.

"Mmmm yeah! Kendra wasn't lying, you're really good at this!"

I reached around and grabbed her ass, pulling her a little deeper into my mouth and squeezing her cheeks. Her balls resting against my chin, I inhaled through my nostrils, taking in the musky aroma that I loved so much.

"Fuck," she sighed. "I'm going to cum...we have to stop, I'm not ready!"

She backed off quickly, not wanting to go over the edge yet, and while panting, she leaned in to kiss me on the lips with a big sexy grin on her face.

"You're a real cock slut, you know that Jay?"

"So I'm told," I laughed.

"Now... I'm going to fuck that sweet little ass of yours too," she said.

She grabbed me by the ankles, and lifted my legs all the way up to her shoulders but slid down some so that her face was right in front of my ass. She spread my cheeks, and I felt her hot breath on my hole as she leaned in and started to tongue my crack.

Up and down along the ass crack her tongue went, lubing up my hole real good. She waited until I was nice and wet from her saliva, before I felt her slowly inserting her index finger. It was no big deal, as it slipped right in with ease and I sighed as I felt her pressing against my prostate. That was only one finger though...

After working her index in and out for a few minutes, Christy slowly inserted a second finger, and I felt myself slowly stretching for her. It still didn't hurt, although it was more uncomfortable for the time being than painful.

Two minutes later, she was slowly guiding three whole fingers into my asshole, pushing them all into me until they were up to the knuckles.

"You're really tight for having been fucked by Kendra."

"It's been a few months," I admitted, "Kendra really stretched me out, and I've been taking some time off from the submissive role."

"Oh really," she laughed, "So I'm the first you've been with since her?"

"Mmhm," I replied.

"Well, that makes me feel kind of special," she giggled.

Christy withdrew all her fingers and went back to licking my hole, which was now spread pretty wide. I wasn't gaping exactly, but I was wide enough, as far as I was concerned, for Christy to proceed.

"I think you're ready to go," she said, as if reading my mind.

She reached over to the nightstand and started digging through the drawer for what I figured was a bottle of lube... after a minute or two though, she sighed in frustration.

"Damn it! They don't have any lube in here."

"Oh... what uh... what are we going to do?"

"Hm... well, I think you're wide enough... we could rely on spit if you're okay with that. I won't make you do anything your uncomfortable with."

I thought it over and it sounded risky. But if she used a fair amount of spit it might not be totally bad, however the only way to determine that was to actually give it a shot.

"Alright," I said nervously, "But... use enough, okay? And be gentle."

"Don't worry Jay, I've done this plenty of times. I can make it work."

Christy had me turn over onto my stomach again, and she smacked my ass. I laughed as she did this a few more times, before spreading my cheeks and leaning in to start licking my hole again. She spent a good two minutes eating my ass, running her tongue back and forth between my asshole and my balls and finger fucking me at the same time.

After about three minutes, she moved around to the side of me and shoved her cock into my mouth.

"Get me nice and wet baby," she said seductively. I sucked, and slurped, deep throating her for about a minute and a half before she backed away,

"That's good enough."

Trusting her, I buried my face in the pillow as she moved behind me again and spread my cheeks. I heard her spit and then felt it hitting my asshole. I thought I was already well lubricated, but I guess it didn't hurt to make absolutely sure. I felt her weight pushing down on me now, and I could feel her huge cock probing at my asshole.

She moved it up and down along the crack for a moment or two before grabbing her dick and pushing it into me. I gasped, biting my lip and gripping the sheets as she pushed all the way into me. Within a matter of seconds, I could feel her hot balls against me, and I knew she had buried all eight inches in my ass.

It wasn't painful at all, to my surprise, just the immediate feeling of fullness was one that I had forgotten in the few months I had stopped being submissive. After the initial shock wore off however, I remembered why I had enjoyed that sensation so much.

Christy waited until she was sure I was alright, then slowly withdrew her cock from my ass until only the head remained inside of me. Suddenly, with zero mercy, she rammed all eight inches back inside of me to the hilt once again.

I gasped again, my body jumping underneath of her as she pulled back once again and repeated the same action. She did this over and over again, pounding my ass, the bed shaking underneath of us as I felt her breasts pushing into my back.

"You're so tight baby," she whispered in my ear.

"It feels so good."

"Oh fuck! Christy...f-fuck me,"

"You want me to fuck you harder sweetie?"


"Tell me... tell me what you want Jay."

"I want you to fuck me... fuck me harder!"

She happily obliged, as she lifted herself about halfway off the bed and dropped back down into me. She grabbed my hips and started slamming in and out of me, flesh slapping against flesh, fucking me as if I had never been fucked before.

This kept up for about three minutes straight, and at this point, my cock was starting to leak pre-cum although it was still not fully erect.

Christy finally pulled out of my ass, and flipped me over onto my back, lifting my legs up to her shoulders and plunging right back in.

"Oh fuck," I shouted, as she rammed back into me and resumed fucking the hell out of me.

In missionary now, she was able to slide much deeper than she had been able to while we were in doggy style. I always preferred to be fucked in missionary, and with Christy, it was no different.

She was now slowing her pace, from a vicious thrust, to more of a gentle fuck and it felt like she was making love to me. Regardless, it felt just as good as it felt when she had been pounding the hell out of me. She started licking and sucking my neck and my earlobe as she had done earlier and then I felt her hand wrap around my cock.

"Look at that baby," I heard her say, breathing heavy, "I may have helped you cure your case of whiskey dick!"

I hadn't noticed until she pointed it out, but Christy was right, my cock was as hard as steel right now. She started stroking me, her hand moving in a blur and continued fucking me at the same time. She trained her lips to my nipples, licking, sucking, and biting gently. My breathing was getting heavier, and I was starting to feel like I might be getting close.

"Hey Jay... wanna see something really cool?"


"Watch this," she said.

She straightened her back a bit and lifted my legs up higher while keeping her cock halfway in my ass. Lifting me up as far as she could, Christy leaned her head in close and right before my eyes she wrapped her lips around my cock and started sucking!

I couldn't believe it... Holly had been totally right. Christy could suck dick while fucking ass at the same time... it was an amazing talent. One that quickly had me shaking underneath of her and moaning a bit louder than I wanted to, as my orgasm rushed through my body. It was the same kind I had experienced from only two other people... Kendra and Annie.

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byWhiskeyIsGood© 14 comments/ 36751 views/ 40 favorites

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