tagTranssexuals & CrossdressersJay's Sex Club Adventures Ch. 09

Jay's Sex Club Adventures Ch. 09

byWhiskeyIsGood©

The day after the party, I woke up in the bed where I had slept with Christy the night before. But I noticed immediately that she was nowhere to be found. I groaned, sitting up and rubbing my head... I had a serious migraine, and my stomach was churning.

The beginnings of one of my typical, yet still hated, hangovers. Certainly not shocking though, considering how messed up I had been. Finally getting a hold of myself, I rolled over and slipped off the mattress.

I found my clothes scattered across the floor, and started picking up each of them and putting them back on again. Once I was fully dressed, I stumbled out of the room and down the hall to the bathroom, relieving my bladder and then making my way downstairs.

"Look who's awake," I heard Annie saying with a hint of sarcasm.

"How you feeling buddy?" asked Lisa.

She was sitting on the couch next to Annie and they were both smiling at me as I walked slowly down the steps. I stopped, and leaned against the wall, rubbing my head.

"Honestly? I feel like crap," I admitted with a grimace, "How about you?"

"I'll survive," Lisa said, standing up and walking over to me. She gave me a kiss on the lips and looked concerned for a moment, "You're sweating like crazy... let's get you some water."

"I got it Lisa, you just sit down and relax," Annie said, jumping off of the couch and rushing to the kitchen.

I plopped down on the sofa and Lisa sat down close to me with her legs pulled up onto the couch underneath of her. She rubbed my arm and smiled at me as I groaned in obvious distress.

"So, who were you with last night," she asked with a wry smile, "I heard you up there... so did everyone else to be honest with you."

I blushed, being slightly embarrassed that what had happened upstairs between Christy and myself had been heard so thoroughly, certainly more than I thought that anyone would realize anyway.

"I was with Christy," I finally admitted.

"Oh," she laughed, "Well that explains all the um... commotion."

"Yeah... that girl can really give it," I chuckled.

"So listen, Jay... I'm hoping to talk to Holly tonight about what I told you last night... about me moving? And I was wondering if you could be with me when I tell her because I know she's going to be really upset, ok?"

I smiled, nodding my head. Of course I'd be there if she needed me... after all, Holly was my friend as much as Lisa was.

"When do you need me?" I asked.

"My place, around eight. Okay?"

"I'll be there," I promised.

Annie returned from the kitchen with a glass of water for me. I drank it down, savoring every drop of the liquid as I felt myself rehydrating.

"So, how is Rob feeling," I asked Annie who laughed.

"Well... you two planned on killing that bottle of Jack together, but he spent the whole night drinking Jager bombs instead. He's still out cold and I expect him to be pretty bad once he does wake up."

I laughed, taking another sip of water. I had lost track of Rob at some point during the course of the night. And as Annie said, it wasn't the two of us who killed the bottle of whiskey as I had originally planned, but rather Lisa and I. In fact, I was really surprised to see her dealing with the effects so much better than I was right now, since we had drunk a pretty equal amount.

"Listen, I should be heading home," I said, standing up and finishing off the glass of water,

"Need to do some chores I've been putting off."

"Are you sure you don't want to stay for breakfast?" Annie asked.

"No, it's okay. I'll pick something up on my way home."

"Let me walk you to the door," Lisa said, taking me by the hand and leading me towards the door.

We stepped outside, into the cool, fresh, October morning air and I turned around to face Lisa. She leaned into me and I hugged her, kissing her on the cheek.

"You don't think she'll hate me, do you?"

"What... Holly? Of course not. Why would she hate you Lisa?"

"I don't know... we've been best friends for years. We're almost sisters, and I just... well, I don't want her to feel like I'm leaving her or something."

"Relax," I said, brushing some hair out of her face and looking into her moist eyes, "You guys will be fine. I promise... okay?"

"Okay," she said smiling. We kissed again and after one more hug I made my way towards my car.

As soon as I got home, I went straight for the shower, bathing in the hot soothing water as it relaxed my muscles. I then grabbed a couple aspirin in an attempt to kill off the headache that had been throbbing in my skull the entire day.

At around half past three in the afternoon, I heard my cell phone ringing in another room. Pushing myself up from the computer desk, I walked out to the living room and picked it up to see who was calling. Only to find out it had actually been a text. And to my surprise, it was a text from none other than Christy.

Christy: Hey cutie. I had a lot of fun last night, and I was thinking if you're up for it, we could start your "lessons" right away. Give me a call when you get this text message.

I barely recalled giving her my number, and actually wondered if maybe she had gotten it from someone else at the party or something like that. Regardless, my hangover was beginning to wear off, and I had been feeling a little aroused for the past hour or so... well, I figured... why not? I dialed the number in the text message and waited as it began to ring.

"Hello," I heard her say as she picked up.

"Hey, Christy... its Jay, from the party at Rob's last night."

"Hey you, I was hoping you would call. I guess you got my text?"

"Yeah, I got it, and yes I'm definitely down for that. Would you like to meet me at my place? We could hang out here and have some fun."

"I would love that Jay," she said seductively, and I felt my cock twitch at the sexy tone she gave me. "I'm not sure where you live though."

I gave her my address, along with brief, yet descriptive, directions on how to get here. After we hung up, and I started moving around the apartment, straightening stuff up the best that I could. I ran to my bedroom, opening the drawer in the nightstand and shuffling through everything inside.

"Shit," I muttered. I didn't have any lube left... that was not good, because we would certainly need some when she got here.

Christy lived about an hour away from my apartment, and I had only hung up with her five or ten minutes ago. I thought I might have enough time to make a really fast trip to the local drug store to grab some things we would need.

Deciding against it though for fear that I would not make it back in time, I grabbed the cell phone and texted her, to suggest that she stop and pick some up.

"I'll pay you back for it when you get here if you like," I mentioned.

I never got a reply text, but when the doorbell rang, indicating that she had arrived, I glanced out the window and saw her standing in front of the door with a plastic bag. I assumed she had gotten what we needed.

"I'm glad you could make it," I said, opening the door for her with a smile on my face. She smiled back, leaned in for a kiss and then I stepped aside to welcome her into the apartment.

"I'm just glad you were willing to meet up again! How's your ass feel?"

"It's okay," I said, shutting the door behind me.

"Surprisingly I thought it would be pretty sore, but it felt better by the time I got home from Rob's."

"I'm happy to hear that; because we're going to be going for a much more intense round today baby," Christy said, winking at me as she opened up the plastic bag and pulled out an extra large bottle of Astroglide, "I got what we needed to make sure things go smoothly like they did last night."

"That's great! Would you like something to drink?"

"Oh, no thanks... maybe after we're done. Could I use your bathroom though?"

I showed her where the bathroom was, and she disappeared behind the door, shutting it and locking it behind her. I took the bottle of lube and walked towards my bedroom, when I heard her calling out from behind the bathroom door.

"Jay, why don't you go get ready in your room, I'll be in, in just a few minutes baby."

I entered my room, sitting the lube down on the nightstand and pulling my shirt over my head. I slipped out of my jeans and boxers, pulling back the sheets on my mattress and laying on my back, spread eagle. I heard the bathroom door open and close, and a few seconds later Christy walked into the room wearing nothing but a pair of black laced panties, and nothing to cover her gorgeous breasts.

I could see the bulge of her cock in the front of her panties, and just looking at the sight before me was enough to get my own cock standing at full attention.

"You look fucking hot," I blurted out. Christy laughed and inched closer towards the bed.

"Thank you."

I spread my legs a little further as she climbed onto the mattress, making it clear that she could go right into things if she wanted. But she stopped right in front of me and shook her finger as if to scold me like a child.

"We'll get to that baby... right now though, I want to see how good you are at giving, before I can determine whether or not I think your worthy of learning my techniques."

"Oh... well I've been told I'm good at being a top," I said, hoping I wouldn't sound too self-centered or anything.

"I've heard those stories, but I want to see for myself. You know, some men... they're just destined to be bottoms. Even if they are good at being a top, the truth is their just better at bending over and taking it like the little bitches that they are. Some men on the other hand, their meant to be tops. And some guys are meant to be both, and they are good at being both. My point is, you really seemed to love when I pounded you last night... and I did too. But to give someone the kind of pleasure I gave you, one has to enjoy being a top enough to really get into it."

I knew what she meant... some guys liked to be both top and bottom, but that did not always mean they really loved one or the other. She wanted to know if I was as passionate with being on top, as I was with being on bottom. Before I could say anything else, Christy moved forward over top of me and started pushing her breasts in my face. I felt my cock straining as she smothered me with her tits, and I breathed in her scent.

I groaned as she reached back and took hold of my throbbing member, and started to stroke me, while I started sucking her nipples.

"Tell me what you want me to do Jay," she said.

She slid down off of me, indicating that she might be heading towards giving me a blowjob.

"Tell me," she repeated.

"I want you to suck my cock, " I said.

"Mmhm, I want to do that too, but I want you to really tell me you want that. Be more aggressive about what you want... more dominant."

She wanted me to demand what I wanted, not ask her for it... I understood.

"Suck my cock," I said in a slightly more firm tone.

"What was that?"

"I said suck my cock, suck my fucking cock."

Without wasting another minute, Christy wrapped her warm, wet lips around my cock and started sucking. Bobbing her head up and down, stroking, licking, rubbing my balls. I groaned, leaning my head back and she grabbed my hand placing it on her head. I pulled at her hair and started thrusting up into her mouth.

"Suck my cock," I moaned as she started picking up the pace.

"Good," she said, stopping for a moment, "Now fuck my mouth."

She lay back on the bed, pulling me on top of her so that I was sitting on her chest. This was a position I had become accustomed to with someone else being the one sitting on MY chest. Now, the roles were reversed. I leaned forward, shoving my cock past her lips and down her throat, my hands on either side of her head above her as I began fucking her throat. She reached behind me and grabbed me by the ass, pulling me deeper into her throat and gagging.

I thrust in and out, with Christy making all kinds of gagging and slurping sounds as she devoured my cock. I really loved the oral attention, but I wanted to progress past that now. I wanted a piece of her ass. I pulled off of her, and flipped her over onto her back, smacking her cheeks and she jumped in surprise.

"Oh yeah," she said. "I like that... smack me again."

I smacked her again, and then spread her cheeks.

"I want to fuck you Christy, I'm going to fuck you really hard. I'm going to bend you over, and shove my cock up your hot little ass. I'm going to make you cum and then I'm going to make you scream."

"Those are some strong words for a bottom," she said, laughing.

"Trust me," I said, "I love being a bottom but I definitely love being a top just as much as I enjoy being submissive."

I reached for the bottle of Astroglide on the nightstand, popped the cap open and poured some down her ass crack. He stroked his cock, lubing that up as well before starting to probe her hole, leaning over her and kissing her between the shoulders. She groaned, and pushed back against him, as his cock pushed into her.

"Oh wow," she sighed, "You feel so good."

Yeah? Well get ready... Now I'm gonna show you what I'm made of," I said.

I grabbed her by the hips and started pounding, slamming in and out of her ass, which I had apparently lubricated just perfectly, because I was sliding in and out as though it were nothing. She moaned and panted underneath of me, gripping the sheets and the pillow as the bed shook. Wanting to show her that I could be a bit more dominant, I pulled her head back, holding it by the hair. She grunted, biting her lip but offered no protest, and so I continued to hold on to her by the hair.

"You're doing great Jay! You really do know how to give it," she said, breathing heavily.

I picked up the pace, fucking her harder and harder and then reached around to grab her cock and start stroking.

"Oh fuck, oh yeah, oh god!"

Her cries of pleasure filled my ears as I jerked her cock and fucked her ass, and I felt her tense up beneath me as her orgasm overtook her. I felt her warm, sticky cum leaking from her shaft, covering my hand and lubricating her cock. I stroked faster, as I felt my own orgasm building and I knew it would be any second now.

"Fuck! I'm going to cum Christy," I announced.

"Good baby, good... fill me up!"

I was more than willing to fulfill that demand, as I buried myself balls deep inside of her, huffing and puffing as I felt my cock swell up and burst. I pumped my load into her, filling her with every drop until I had nothing more to offer. When it was over, I slipped out and dropped down onto the mattress next to her and she moved close to me.

"That was so... fucking good babe," she said, still a little out of breath, but obviously very impressed.

"Now, let me remind you how a real top does it."

She didn't wait for a reply, before lifting my legs all the way up over my head and applying lots of lube to my asshole. She slipped a finger into me, massaging my prostate gland, taking her time to get me worked up really good. There wasn't a lot of preparation to be done, since I was still kind of loose from the pounding she had given me the night before, at Rob's house. So once she was sure I was ready, she held my legs in place and pushed her massive prick right into me.

I gasped, the immediate feeling of fullness, taking me off guard. I had forgotten that she was nearly as big as Kendra, and I had not braced myself at all before she had entered. I adjusted quickly though, and soon enough, Christy was thrusting in and out of me with ease. "You're really loose from last night, but your ass still feels so good."

"God Christy! I love your big fat cock in my asshole."

"See that," she said, smiling, "That is definitely not something a true top would ever say, now is it Jay? I can see, you love being a top...but I think you enjoy being on bottom just a little more."

She pulled out, and flipped me over onto my hands and knees, smacking my ass hard, before thrusting back into me. She started fucking me really hard now, pounding the life out of me and shaking the bed violently. She slapped my ass again as she fucked me, and demanded, "C'mon... say it!"

"Agh!"

"Tell me Jay... tell me you love to be fucked like a little slut."

"I d-do," I stammered, my body beginning to tremble underneath of her. "I love... being fucked... like a slut."

"Good boy," she whispered, slowing just a bit.

"Now I'm going to teach you some new tricks."

She changed positions once again, pushing me onto my back and lifting my legs all the way back to the point where I was looking up at my own dangling cock and balls. Christy pressed her cock to my hole, and plunged back in, immediately pounding me with no mercy. This was the anal pile driver and she was really going all out.

In this position though, Christy seemed to be able to reach exactly the right spot, and within seconds, I was shaking underneath of her. Sweat ran down my chest and face as she continued pounding me in the same position. My neck and back began to hurt a little, but the pleasure outmatched the discomfort, and I offered no protest.

I felt my orgasm beginning to grow closer and closer as my cock started to swell right in my face. I gasped, then cried out in pleasure as my entire body went into that familiar fit of spasms. Then, taking me completely off guard, my cock exploded, shooting cum all over my own face and chest... some of it even managed to get in my mouth, almost making me laugh.

"Wow, I bet you enjoyed that, didn't you," Christy teased, "Look at you, and all covered in your own cum... such a dirty boy!"

She resumed pounding me really hard, but then suddenly stopped and withdrew, allowing me to slide back on the mattress, out of the pile driver position. She had me spread my legs again, but not quite as high as before, and eased her cock back into me. She was moving much slower now, gently massaging my sweet spot with her erection.

I wasn't sure what she was trying to accomplish. I had already hit my orgasm, the only thing left now was for her to cum... but she had different plans. Christy leaned in and started licking my nipples, my body was twisting and writhing in pleasure underneath of her. They were both very sensitive at the moment and she took full advantage. To my surprise, my own cock began to rise once again, quickly becoming as hard as a rock.

Once she saw that she had accomplished her goal, Christy picked up the pace again, thrusting in and out of my ass with no mercy.

I reached for my cock to stroke it, but she swatted my hand away, and grabbed hold of it for me. She pumped my dick with her hand, fucking me harder and faster, and I was building towards yet another orgasm. Then, just like last night, she lifted my ass off the bed and wrapped her lips around my cock. Christy started sucking, stroking and licking, slurping and gagging on my dick while fucking my ass in perfect unison.

"Ohhh... holy shit!" I exclaimed as I felt myself losing control yet again. This was probably the hardest orgasm I'd had so far, as I emptied every drop of cum from my balls.

By the time it was over, I was sure I had cum so hard that I would be literally semen-less for the next few days.

I was also amazed that she had swallowed all of it, not losing even a drop. Once I had finished my orgasm, Christy decided she was done milking me and now it was time for her to get herself off at last. She started ramming in and out of me, moaning and whimpering in my ear, making all kinds of sexy noises.

I felt her swelling up inside of me and I pushed my ass against her, wanting her to fill me up so badly. She finally did just that, erupting almost as hard as I had a few minutes earlier, and pumping her hot sticky cum deep inside of me.

She collapsed on top of me, exhausted, breathing in my ear as I wrapped my arms around her and held her close. When we both recovered, Christy pulled off of me and lay down at my side, both of us staring up at the ceiling, trying to get our thoughts together.

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