tagTranssexuals & CrossdressersJay's Sex Club Adventures Ch. 11

Jay's Sex Club Adventures Ch. 11

byWhiskeyIsGood©

A whole month had passed by since Lisa and Holly had moved into my apartment with me, and both girls were now definitely settled in. Things had gone a different route then we originally planned though, with Lisa moving into my bedroom and sleeping in the same bed with me, and then Holly took the room that was originally supposed to belong to Lisa.

I wasn't sure at first how to look at the fact that we were both sleeping in the same bed together. It certainly made things look like something other than what they actually were. On one hand, Lisa and I agreed months ago that we were in a sort of friends with benefits type relationship. I had adjusted to that idea and I had definitely gotten comfortable with it... until recently.

On the other hand, now that we were sleeping in the same bed together, I really didn't see that as the sort of thing that friends with benefits did. I saw it as something a couple did, and that it was something that crossed a line once you started doing it. I hadn't brought this up to her yet though, and honestly, I wasn't so sure I wanted to because I was afraid I would just get the same response I had the last time we spoke of it.

It was nearly Christmas, and the end of the year was just a couple weeks away. That meant Lisa would be leaving soon. She planned on leaving January third, which now felt so much closer than it really was, and I found myself dreading that day terribly.

Things at The Raven were really starting to heat up during the holiday months. Thanksgiving was the start of it all, with a lot of special events and parties, specials on most alcoholic beverages of course. Then December had been packed with lots of fun events, even more than November was.

Recently, the DJ quit, taking a job at another location. Of course this meant that The Raven needed a new DJ. Lisa stepped up to take that role... at least until she would be leaving for her mother's house... and she really seemed to be having a lot of fun with it too.

Tonight was the clubs big Christmas Party, taking place on December 24th, Christmas Eve. There was sure to be a lot of people packed into the club, and I was definitely going to be there as well. I was also sure Rob and the others in our little 'gang' would be there and it was sure to be a fun time. Unfortunately, Holly could not go, because she was stuck at work. That was such a bummer to realize she couldn't make it, but there was just no way around it really.

I arrived at The Raven around nine to find Rob, Annie and Jen already sitting at the bar, having a few drinks. The dance floor was packed, with lots of people, loud music, and dirty dancing.

The rooms in the basement, from what I heard, were all occupied with a lot of people having fun together... it was promising to be a very busy night.

The club was well decorated, with all types of Christmas decorations set up all around the place, and some people had even come in dressed up in Christmas costumes. I took a seat at bar, next to Rob and Annie, and ordered a beer.

"Good to see you again Jay," Annie said smiling at me, "How are you and the girls settling in at your new place together?"

"Things are going great Annie," I replied, smiling back, "Thanks for asking!"

"Where's Holly, dude," Rob asked, searching around behind me.

"She really wanted to be here, but got stuck at work. They had a few call outs so they really needed her to stay for the rest of the night."

"That sucks," Jen chimed in, "I was looking forward to seeing her tonight."

I was disappointed that Holly wasn't here, and I knew Lisa was too. But the party must go on, as Holly had insisted. She wanted us to do our best to have fun anyway. After about an hour passed, and I decided it was time to go check on Lisa and say hi.

I stood up from the bar and walked off to the bathroom to relieve my bladder. But after returning, I decided that before forcing myself to walk across the dance floor, while pushing my way through the crowd of sweaty dancing couples and friends. I would just skirt around to the DJ booth located on the far left hand corner of the club.

Looking like something from a Wizard Of Oz movie set, a curtain separated the DJ booth from everyone else. This was an arrangement Lisa was happy with, since it gave her privacy, and let her hang out with people behind the scenes without interruption. I walked over and poked my head inside, all the while resisting my compulsion to say 'ignore that man behind the curtain'!

Lisa had a nice set up, on a small table in front of her were two laptops running everything. One of the them was hooked up to an amplifier, with iTunes pumping the dance music out for the club.

The other laptop was her personal computer and had her Facebook page pulled up along with her e-mail waiting on a separate tab.

A Smirnoff wine cooler sat waiting on the table between the laptops, while a hot looking Lisa sat waiting just behind it. Wearing her newest Christmas lingerie. She had on her red velvet bra with white fluffy trim that was just barely hiding anything, along with a pair of red velvet panties and a Santa Claus hat that also had plenty of the snow-like fur added to the get-up.

Adding fuel to her fire, she had on red nylon stay-ups and a pair of red patent leather 4-inch heels... damn, did she look sexy.

"Knock-knock... mind if I join you?" I asked with a smile.

She jumped in surprise, then stood smirking for a moment, before she quickly stepped towards me, grabbing me by the arm to pull me inside and closed the curtain. Our lips crashed together, kissing passionately, and our tongues began an intense wrestling match as my arms wrapped around her.

"Mm... I'm glad you're here now," she said seductively.

"It's a shame though," she pouted, "all the rooms downstairs are in use."

"It's not like you could leave your little area here anyway, right? I mean, who would maintain the music and all that stuff?"

"Yeah, you have a point," she agreed, disappointedly, "But... I suppose we could have our fun here... if we really wanted." She winked and I laughed, pulling her closer, kissing her again.

Just breathing in her scent was intoxicating and I immediately felt myself getting hard.

I stepped back, looking her sultry body over again, sighing hard, with my cock raging for release, "Did I mention how fucking hot you look tonight?" I moaned in her ear.

"Why thank you," she giggled, then in a low sexy voice said, "So...what do you say? Wanna have some fun?"

"Don't I always," I joked.

We started kissing again, and her hand went down towards my groin, rubbing my cock through my pants. I moaned into her sweet kiss, reaching out and massaging the bulge I knew she had for me in her red Santa panties.

"Mmhm, Mrs. Claus has a present for you," she winked, motioning down towards her stiff cock as I laughed, slowly getting down on my knees in front of her.

As I pulled her panties down, she lifted her legs out of them, before I threw them to the floor. Her hard cock was standing at full attention now, and I went to work, teasing the head with my tongue.

I could taste her strawberry scented soap that she always used to shower before coming out for 'fun', and I licked and teased her cock before swallowing her entire length. She was moaning now, grabbing my head and forcing her dick all the way down my throat. I started to deep throat her, sucking with passion, and reaching up to pinch her nipples under her bra.

"Ooh fuck Jay... that's it baby. Suck my fucking cock."

I increased my passion, eager to make her feel good, and it was certainly having the right effect. She started thrusting in and out of my mouth, her balls pressing up against my chin, treating my mouth like a wet pussy.

I inhaled the musky aroma of her balls and began moaning myself, with my own cock now straining inside my boxers as her scent was turning me on even more. What a little cock sucker I had become ever since I met this girl... and I loved every hot second of it! Suddenly I had to stop sucking as she lifted my head up to look up at her. She smiled down at me, stroking my cheek.

"Now, tell Mrs. Claus what you want for Christmas baby."

"What I really want? Well, I would love to have you on your knees sucking my cock right now."

"Oh, is that so? Mmmm, I suppose that can be arranged," she purred.

Pulling me to my feet while showing more strength than I'd ever seen before, Lisa quickly shoved me down into the small chair behind me. She then dropped to the ground in front of me, while pulling my pants down. My cock sprang free as she immediately swallowed it whole, wasting no time going to town on me.

Up and down her beautiful head bobbed, her wet lips gliding skillfully over my shaft as she sucked and stroked me into oblivion. We kept that up for another few minutes before I slid off of the chair, and we started making out again.

Somewhere about now, she placed her hand on the middle of my back and pushed me down onto my hands and knees, spreading my ass cheeks as she positioned herself behind me.

I felt her fingers skimming over my hole as she slapped my ass twice, laughing as I jumped. But now I felt her face between my ass cheeks, with her hot breath against my hole, she started licking, nipping, and eating my ass.

I groaned, grabbing my cock, while starting to stroke myself as she had her fun behind me. After a couple minutes, I decided to reverse things. I straightened myself up, turned around, grabbed her by the hips and set her down on the edge of her little table.

Squealing... giggling... loving every second as she always did when I would reverse positions like this, I now pushed her onto her back, lifting her legs, I licked and sucked her balls, moving my tongue down her ass crack and pushing it into her hole.

"Mmmm... that feels so good baby," she whispered hoarsely.

I continued my rim work as she groaned and writhed on the table, wrapping her legs around my neck and pulling my face deeper into her ass crack.

Finally, she pushed me away and slid off the table, getting on the chair and leaning over the back of it with her ass pointing out towards me. I got behind her and continued to eat her asshole, reaching around to jerk her cock at the same time.

I wanted to fuck this woman so badly... more than I could ever remember wanting such a thing before, I wanted to thrust my cock deep into her ass and pound her as she screamed my name. All of this was running through my mind as I lubed her with my tongue, but then suddenly I was just standing behind her... mesmerized, rubbing my cock against her hole, watching as her cock twitched harder with each and every heartbeat.

"Jay?" she whispered, then finally broke the spell exclaiming, "JAY! Don't tease me... that's mean."

"Sorry my love... I... It's so... so wild to see you... so excited for me."

I rubbed my cock against her once more before grabbing her by the hips and slamming myself deep inside of her. She moaned, biting her lip and gripping the back of the metal chair with all her strength as I began fucking her.

Thrusting in and out, my cock was pounding her ass with long hard strokes while Lisa cried out and moaned in pleasure every time I drove myself deep into her. We kept it up like that with me fucking her from behind for about a few exciting, but still tiring minutes, before I pulled out and she got off of the chair.

I took her place, sitting down to take a break, and her lowering her ass down onto my cock in reverse cowgirl style with her back facing me.

Again, I grabbed her by the hips, and she began bouncing up and down on me, riding my cock. Her own dick flopped about as she moved up and down on me, and my hands moved from her hips up to her breasts and started to massage them.

She reached down and took hold of her shaft, and began jerking off as she started grinding against me. I felt my balls starting to tighten up, my cum building up inside of me... getting ready to blow.

"Oh fuck," I gasped, "I'm gonna cum Lisa... I'm gonna cum!"

"Mmhm, yeah baby! Cum for me, cum in my ass, fill me up with your load."

I let loose, yelling so loud that despite the blasting dance music, I was sure if anyone were standing near that curtain they would've heard me.

My cock exploded deep inside of her, cum spurting deep into her ass and leaking out and down along the length of my shaft. Lisa chuckled, grinding against me, milking every last drop from my balls before I sank back into the chair, my body spent.

She sighed, pulling herself off of my dick and while my cum still streamed down the back of her leg, she shoved her ass up in my face.

"Go on baby, clean me up." She insisted.

I groaned as she shoved her ass right up against my face, and I was forced to lick her gaping hole, tasting my own cum. I licked her clean, as she backed away and then turned around to face me, stroking her own dick right in front of me.

"You know baby," she said, "I haven't cum yet... wanna finish me off?"

"Of course," I replied, pulling her towards me.

I never considered it a good sex session unless both parties got off in the end. If I blew my load, and my partner still hadn't come, Then it became my responsibility to make sure that they got off. Otherwise, it just wouldn't feel right.

I wrapped my mouth around her dick again, sucking her back deep into my throat and slipping a finger into her wet asshole to rub her prostate. She cried out, squealing once again as her dick swelled up in my mouth and erupted, shooting her cum all the way down my throat. I swallowed every single drop, and then licked her clean, all before coming up for air.

I stood up and buried my face between her breasts, licking and sucking her nipples. She now massaged my temples as she softly kissed my forehead while sighing.

"Oh god Jay... you are incredible. I never get used to how passionate you can be sometimes. You have no clue how good you make me feel babe."

I smiled, happy to hear her say such a thing, and I kissed her on the lips. We started putting our clothes back on and I thought about what she had just said to me... I wondered if that was her own way of telling me what I'd wanted to tell her. I didn't know for sure, but it sounded like it could have been.

The more I thought about it though, the more I started to doubt myself... if we were falling in love with each other, why be so subtle about it? Why not just be straight forward about what we both wanted to have in the end.

I looked at the clock, it was almost two in the morning. The Raven would be closing soon, and Lisa and I would be heading home for the night. Once we had all of our stuff back on, Lisa announced over the microphone that the night was coming to an end and for everyone to be safe going home and enjoy their Christmas the following day.

When the announcement was finished, she shut off the computers and after we helped clean up a bit, within forty five minutes we were on our way home to our apartment.

When we got home, Lisa and I settled in for the night, and before long we were both wrapped up under the sheets in our bed. Holly had made it home alright and was already fast asleep in the room next to ours. Our apartment was silent, and yes, not a creature was stirring, not even a mouse, as I laid my head down on the pillow next to Lisa and sighed.

I couldn't stop thinking about the feelings I had for her. They were becoming so much harder to keep inside. I wanted to come out to her about it, more than anything. I feared rejection though, and so I kept my mouth shut, if she did not share the same feelings, if I was the only one who wanted to take this beyond a friends with benefits relationship, I might actually ruin what relationship we had.

These thoughts weighed so heavily on my mind that I knew it would take me hours to fall asleep. But while I was fighting back these fears, a single tear managed to push its way onto my cheek. It seemed I'd lost this round, as it silently trickled onto the pillow between us. Lisa on the other hand, had fallen sound asleep in my arms just minutes after we first laid down together.

Finally, morning came and I was awoken to the sound of Holly calling my name. My eyes struggled to open, groaning as I sat up on the bed to find her leaning over me with a big sexy grin on her face!

"Morning sleepy head," she laughed.

"Uh... g'morning," I replied, still trying to wake myself up.

"Merry Christmas sweetie, come on out to the living room. Lisa is making breakfast before we open presents by the tree."

I sighed, sitting up as Holly climbed off of me and took me by the hand, pulling me off the mattress and leading me out into the living room. Sure enough, Lisa had made a nice bacon & eggs breakfast, and the three of us sat down at the table to eat together.

After we finished eating, we got to the part of Christmas that all of us had been waiting for, exchanging presents! Lisa and Holly had both pitched in together and apparently bought two different presents together for me. I laughed as they eagerly shoved the first one into my hands... it was a kind of a long shaped item, gift wrapped, and pretty heavy.

"I wonder what this could be," I said, sarcastically. I had a feeling I knew already what was inside this box and if I was correct, I wasn't going to be able to resist laughing.

I tore open the wrapping paper, and sure enough, I found in my hands a seven inch dildo.

The girls laughed, as I smirked at them both, shaking my head and holding the sex toy up in front of me.

"Well-well, what DO we have here?"

"To keep you company when we're not here to have fun with," Holly said, smiling.

"We also figured it might help you get used to being the bottom slut that you seem to be turning into... practice makes perfect," Lisa joked.

"Well, I didn't think I needed much practice," I laughed, "I mean hell, I've already taken Kendra and Christy, I'm getting used to big cocks."

"Here," said Holly, handing me my second present.

This one was square shaped and not very heavy, and it felt like whatever was inside might be some sort of paper item. I ripped open the packaging and found myself looking down at a large calendar with a beautiful blonde on the front... but not just any ordinary blonde.

She was spread eagle, and between her legs where I would have expected there to be a pussy, there was instead a large, fully erect cock.

"Wow... Nice one," I laughed.

"Their all top shemale models," Lisa said, "Very sexy too."

"We both figured you'd like that one," said Holly.

"Definitely! I'll hang it up right away."

I quickly stood up, snatching two boxes from under the tree and quickly handed them Lisa and Holly. Both girls smiled as they started unwrapping their gifts. Well, Lisa unwrapped hers. Holly, on the other hand, tore hers open like a 5 year old kid who couldn't wait to see what was inside.

Holly started laughing excitedly as she freed her gift from its wrapping paper, and held it up in the air. I had gotten her a new iPod that I knew she had been wanting for quite some time now. I even made sure it was her favorite color, red, and that there was a LOT of space on there for plenty of music. She stood up, walked over, and gave me a big hug and a kiss on the cheek.

"Thanks Jay, I love it!" she gushed.

"No problem Holly."

I watched as Lisa finished unwrapping hers, and held up the small black velvet box... inside was a golden locket with chain, that could open to display a picture or small memento. I picked it up at a jewelry store when I was down in Center City a few weeks ago. I knew the moment I laid eyes on it, that she would love it. And now I could tell by the look on her face that I was absolutely correct.

"Jay... this is... so beautiful," she said, her eyes welling up as she smiled over at me, "You really... this is... you didn't have to do this."

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byWhiskeyIsGood© 12 comments/ 13674 views/ 17 favorites

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