Jay's Sex Club Adventures Ch. 19

"Now there's an idea," she laughed, "I've had a taste of your ass plenty of times. But Jen's always been a bottom. Doesn't mean she's never been curious."

"Really? Has she ever said... well... you know?"

"Once or twice," she answered. "With all the

gossip floating around the Club about what a good ass you have... it's only natural that it would cross her mind at least a few times."

That's right, the few times I'd been with Jen, it had always been me topping her. She was a bottom, and never expressed much interest in switching roles. But apparently, she was just as curious as any bottom to see what it was like to top, maybe tonight she would get a chance to change things up.

As we arrived at the apartment, I felt my cock begin to rise again in my pants, despite having just gotten off a few minutes earlier thanks to Holly. It was safe to say this much anticipated threesome was probably going to be a LOT of fun.

We made our way up the stairs and into the apartment to find Jen sitting on the couch, smoking a cigarette and watching TV. She looked over at us as we stood in the doorway, and Holly smiled, tugging at my arm.

"Jay here has decided he's ready for that threesome that we offered him a few weeks ago."

"Oh really," Jen said, sounding excited as she shut off the TV, set the remote control down, stood up, and quickly put out her cigarette to walk over next to Holly, "well I was starting to think you were never going to get back to us on that one Jay. God, you have no clue how badly Holly and I have wanted this."

"Sure would have happened sooner, if I hadn't been so busy lately," I said, knowing that most of why I hadn't been over here was because of all the work I was doing on the house.

"We understand," Jen smiled, "but you're here now babe. So let's help take off a little bit of that stress, shall we Holly?"

"Yeah... let's," she replied, seductively.

Both girls took one of my hands and led me through the living room and down the hallway towards Holly's bedroom. As we stepped into the bedroom, Jen led me over to the bed while Holly closed her door and locked it, then watched as her friend gently pushed me onto the soft mattress. Jen licked her lips seductively, and my cock was suddenly as hard as it could possibly get.

Holly stepped alongside Jen, and in the low light of the bedroom the two girls turned to face each other. Both giving an incredibly sexy smile before they started kissing. For me, nothing could be as hot and beautiful a sight, as watching these two gorgeous women make out in front of me. Their hands were now roaming over each other's bodies with Jen sliding hers under Holly's shirt to feel her breasts and soon they were starting to undress each other.

I took their queue, sitting up a bit as I pulled my shirt over my head, tossing it onto the floor, and quickly undoing my belt to slip out of my pants. Now that I was down to my boxers, I watched as Holly started kissing Jen's neck, down her collarbone and began licking her breasts. She moved further down below her waist, teasing Jen's cock with her tongue. Holly's eyes moved in my direction and with a beautifully innocent look, swallowed Jen's cock between her lips and was sucking and swirling her tongue around Jen's hardened member.

Holly continued performing some very intense oral on Jen, and just as Jen looked like she was about to blow her load, backed away from her on her knees and sighed, as if trying to hold back the inevitable and explained.

"You wanna taste," asking softly while smiling over at me.

"What kind of question is that," I laughed, "of course I do."

Both girls were giggling as Jen crawled onto the mattress, sliding up next to me until she was right alongside with her cock pressing against my cheek. I turned my head to face her, and she started slapping her dick against my lips, teasing me.

I could see Holly over in the corner, sitting on a chair, stroking her own cock as she watched Jen slip her throbbing member between my lips, shoving it deep into my mouth, and I gagged as she started thrusting in and out, fucking my throat.

"Oh, yeah that feels great," she moaned.

She pushed deep into my throat and held herself there for a few seconds, before backing off and sighing heavily. I noticed Holly making her way over now and joined us on my other side, both girls now over me with their cocks in my face. They shoved their dicks into my mouth together tag teaming me, and I tried my best to accommodate both at the same time.

As they were shoving their cocks down my throat, they leaned in close to each other and started making out again on top of me. I could look directly up at both of them as I sucked them off. I started moaning really loudly, as my own dick became hard as a rock at the events taking place right on top of me.

"Hmm, looks like Jay's enjoying himself as much as we are," said Jen with a sexy grin.

"I knew he would," Holly smiled, "we talked about it in the car, and if you still want a piece of that ass of his... he said he'd be more then willing to let you have a go at it."

"Is that so, Jay?"

"Mmhm," I said, my voice muffled by their hard cocks in my mouth. The girls laughed as they each pulled their dicks out.

"That was a yes I suppose?" Jen asked.

"Oh definitely," I replied.

"Cool. Turn over onto your hands and knees," she instructed.

I did as Jen told me to do, rolling over into the familiar position with my ass up and my face down as Jen got behind me and gave me a slap on the ass. Holly handed her a bottle of lube, and I heard the cap popping off and the sound of the lube being squirted onto her cock. A few moments later, I felt the cold lube pouring all over my asshole as Jen started rubbing it in, and sliding her finger into my hole to loosen me up a bit.

"While Jen's enjoying that sexy ass, I'm going to continue enjoying your mouth, if you don't mind Jay," Holly said.

She came around in front of me, and we smiled at each other as she ran a hand through my hair and shoved her cock back into my mouth again.

I could feel Jen's cock probing my ass as she ran her hands up and down my back. Then with one swift move, she pushed her dick into my hot ass and I groaned against Holly, slumping forward some, my mouth sliding further over her dick.

"Oh wow," Jen moaned, "Holly was right, you feel incredible around my dick Jay. God, I love this."

She grabbed my hips and started fucking me, slowly at first as she was trying to keep it going for as long as possible. Every thrust that she delivered into my ass, pushed me forward, and more of Holly's cock would slide into my throat. I was in the middle of a spit roast now between Holly and Jen and it was beautiful.

Eventually, Jen decided she wanted to switch positions and fuck me missionary style. Holly was fine with it since that meant I could continue sucking her cock. I was turned over onto my back, my legs lifted up and Jen thrust her cock right back into my asshole. Holly was on her knees over my face, and her cock was sliding in and out of my mouth as the two girls continued to have their way with me. They leaned in close to each other once again, and again started making out right above me.

Never growing tired of this, I once again felt my cock starting to ache and the familiar feelings of an orgasm approaching. My body started to tremble, my ass clamping down around Jen, and moaning loudly around Holly as my own dick explodes, spewing cum all over myself. I shot off about six or seven strings of thick white cum, and they went pretty high into the air too earning a laugh from Holly and Jen.

"Whoa, somebody really enjoyed that," said Jen.

"Oh fuck," I sighed, coming back down from my orgasm.

"My turn now," said Jen.

Holly backed off for a moment as Jen leaned into me, my legs wrapping around her and pulling her cock deeper into my ass. She started really pounding me now, with long hard strokes, the bed shaking underneath of us.

We were both grunting and moaning and I could feel myself starting to shake once again, as a second orgasm crept in.

"Oh fuck, yeah, oh shit," Jen moaned.

Slamming harder and harder into my ass until finally I felt her starting to swell up inside of me. With one final, powerful thrust... she buried herself inside of me and erupted. I could feel her cock pulse and I knew her hot, thick cum was filling me up.

She collapsed on top of me, exhausted, and laid there like that for a few seconds before pulling out and rolling over next to me.

"Hah," she laughed. "That was fucking great. If I had known it was that much fun, I would have topped you long ago."

"So, you switching sides now," asked Holly.

"Nah," she replied, nonchalantly, "I still love being submissive. But I may be mounting a few more guys every so often in the near future... count on that much anyway."

We all laughed. Holly who was now sitting beside me, started running her hands through my hair, a smile on her face. Jen noticed, and sat up, smiling at the both of us.

"Listen... I um... I'm gonna leave the two of you to yourselves now," she said quietly, rolling out of bed and making her way to the bathroom.

"We had fun," Holly called after her.

"Likewise... and thanks," she replied over her shoulder.

I looked over at Holly, and she looked back at me, and we couldn't help but laugh. Not at anything in particular... we just started laughing. As I lay there chuckling softly, she crawled up closer to me and rested her head on my chest. Softly kissing my cheek, another on the lips, as I felt her hand trailing down my stomach towards my flaccid cock. Her hand wrapped around it, and begin pumping up and down, stroking me slowly until I was getting hard once again.

Suddenly we were passionately making out, moving her legs over and straddling me, the head of my rock hard cock was now pushing at her ass. She leaned in and gave me a hot, soulful kiss, while pushing down on my cock until I slipped into her. I moaned, gripping her by the hips as she proceeded to ride my cock, slowly at first, bouncing up and down on me. Then gradually started moving faster, as the bed creaking underneath of us, and the sound of flesh slapping against flesh, echoed through the room.

As aroused as anytime I could ever remember, I flipped over on top of her, wrapping her legs around me and my cock slipped deeper into her ass as I started pounding her with long hard strokes. She moaned softly, digging her nails into my back and biting my neck as I continued to fuck her deeper and harder.

Reaching an incredibly intense climax, I emptied my load deep into her as she screamed out in pleasure, her own cock spewing cum all over us, both her breasts and my stomach. I gently pulled out and laid down beside her as we spooned into each other, I held her in my arms and she pulled my arms even closer. We stayed like that for a long time before I felt her breathing slowly calm, and knew she was asleep.

It was then that I realized, watching her sleeping peacefully at my side, that we had not just fucked as usual... we had made love. There was something so much more passionate about it that time than there usually was it... it just felt different, and I didn't know how to wrap my head around this new feeling.

But that confusion suddenly started to give me a headache, I slowly slipped out of bed, being as careful as possible, so as not to wake her. I put on my clothes, slipped out of the apartment, and drove back to the house in New Jersey.

And during the entire drive back out there, she was all I could think about... what had happened between us after Jen left the room? Here I was, setting up my first house that I had ever owned, and I had every intention of settling down with an older transgender woman... and now...

I was starting to feel things for my best friend that I never imagined I would possibly feel, and yet the feelings were there, and had been there for some time now. Perhaps my confusion was because the feelings that I thought I had been developing for Christina had actually always been there... but for Holly. So who did I love... Holly or Christina?

By the time I pulled into the driveway at the house, I knew one thing for sure, there was no way I could have them both. I saw Rob's car was already there and sighed heavily as I shut the door to make my way inside. I found him passed out on the couch in the living room, beer bottles were all over the coffee table, but I certainly couldn't be angry that he was knocked out. It was a good deal later than the time I said I would be back and he probably needed the rest anyway. We would resume working on the house again first thing tomorrow, so I left him to sleep.

I walked up the stairs, and into the room that had been my Uncle's, but was now mine, and was surprised to find Christina sound asleep in my bed. While I hadn't been expecting her over tonight, I didn't pay it a whole lot of mind... I had, after all, told her that she could come over any time that she wanted.

I stripped down to my boxers, a little too tired to bother taking a shower, and crawled into bed next to her with my back facing her. I stared at the wall to the left of me for a long time, thoughts of Holly still weighing heavily on my mind as I fitfully dropped off to sleep.

I woke the next morning to the sound of my ringing cell phone. Lifting my head up off the pillow, I grabbed the phone and saw that the caller ID read 'Holly'. I pressed the talk button and put the phone to my ear.

"Hello?"

"Hey you," came her beautiful voice. "What time did you leave last night, I woke up and you were gone."

"Uh... not long after you fell asleep. Sorry, I just... didn't want to wake you so I tried to slip out without being too loud."

"It's no problem," she said.

Her voice was cheerful, and I loved when it sounded like that. Suddenly I realized it hadn't sounded like that for some time, but I was pretty sure I knew why it sounded that way now. And I really wasn't sure if it was such a good thing at the moment. I knew we needed to discuss what had happened, and apparently Holly felt the same... because she beat me to it.

"So um... about last night," she started, "You and me... ya know, after Jen left... that felt um... well, a little different from what we're used to, didn't it?"

I hesitated, rubbing the sleep from my eyes and nodding my head even though she couldn't see it through the phone.

"Yeah... yeah, it was... definitely very different."

"So you felt it too, then? That spark... we clicked... right?"

I smiled weakly and sighed. "Yeah... I felt it,"

"What's the matter?" she asked, sounding concerned, "You don't sound all that happy about it."

"Holly, l-listen... I um..." I was stuttering now, as this was not going to be easy for me, "I really don't want to make too much out of it... whatever it was last night. I mean... I can't lie... I did feel something. I just... I don't want to take a chance and ruin a friendship that's taken so long to build, you know? And... I'm with Christina now anyway. Things are just getting serious, slowly but surely, and I don't think... well..."

"It's okay," she interrupted, "Jay... really... I understand."

I knew... the sparkle in her voice was suddenly gone and I felt like an absolute piece of crap. What the hell was wrong with me... seriously? I sounded like a total asshole the way I was talking to her right now and I knew it.

"I see... I completely understand Jay. Listen, I just wanted to let you know you can give me a call when you're ready to go looking for the kitchen for the house and I'll meet you wherever you are going shopping for it. Sound good?"

I knew that wasn't why she really called, but I played along and said okay. With nothing else to say on either side, we said our goodbyes and hung up the phone. I fell back against the pillow and sighed heavily, cursing myself silently for being such a prick. I was just very, very confused at this point.

I got out of bed, and put on some clothes, stopping off at the bathroom before making my way downstairs. I found Christina in the kitchen cooking breakfast, two cups of coffee already set out on the table, one I assumed being for me. It was things like this that showed me that Christina was a good person, and that's why I loved her... or at least...

I had been thinking that I was in love.

"Morning babe," she said, from the stove as she worked on the eggs and bacon she was cooking.

"Morning," I replied, sounding drowsy and depressed. I plopped down into one of the kitchen chairs and took a sip of coffee. Christina glanced over at me and notice that I looked a little upset, and walked over to me.

"What's wrong?"

"Hmm? Nothing," I said, shaking my head and putting on a fake smile, "Breakfast smells great you didn't have to do this."

She smiled and gave me a kiss on the cheek.

"I know," she said walking back over to the stove, "I just wanted to, besides... Rob left early this morning... Annie needed him to help her run some errands. So, it's just you and me for a few hours before I have to take off for work."

She finished cooking, preparing us both a plate of food and sat down across from me. We ate in silence... it was uncomfortable as I tried to keep the illusion that I wasn't bummed out over anything. When we finished, I sat there while she placed the dishes in the sink... then came back to the table and sat down across from me again.

"Jay..." She said, calmly trying to begin a conversation, when it became obvious I couldn't, "if this is about last night, I already know what happened."

"W-w-what?"

"I know that you and Holly and Jen had a little threesome."

I searched her eyes, trying to figure out if this was going to turn into a very bad conversation, or if she was just acknowledging it and wanted to let it slide. Then she smiled, resting her chin on her hand for a few seconds before speaking up again.

"It's alright Jay," she said to my surprise, "I... I'm not angry. I know you and Holly are close, and I know you've been with Jen a few times in the past. Plus Rob and I had a long talk, and told me they had been offering you a shot at the both of them together for a while now... fair is fair."

"You... you're... not angry," I asked.

"Not at all... it's really okay. But, I was wondering... have you thought about what I asked you the other day? You know... about settling down I mean?"

I didn't give an answer right away, and a few moments of silence passed by, the tension between us now building slowly into an almost painful pause. Not because she was getting impatient, rather because I was still trying to make up my mind about it all... I was wondering once more if I had made the right choice during my phone call with Holly an hour ago.

"Yeah, I thought about it."

"Good," she said, "Now... can I ask you something?"

"Sure."

"I've heard... from some of your friends, that you and Holly have always sort of had this spark between the two of you. A lot of them seem to have thought... well, that you two would wind up together. She's a nice girl... closer to your age... and you are practically best friends. Jay... I think I need to ask you... are you in love with her?"

I froze, once again finding myself unable to figure out what to say. I wanted to scream suddenly... why was it so difficult... I sighed, burying my face in my hands, and trying to ignore the huge headache growing between my temples. I heard Christina sigh as well, and the sound of a coffee cup being set down on the table across from me.

"Jay... I think we should take a few days apart. And maybe you can find an answer to the question that I just asked you. You seem very confused, and honey... that's not healthy. If you come back to me and the answer is that you do love her, well I'll leave you both in peace. I won't resent her or be angry with you... or anything. Because in the end, I just want you to be happy. What I don't want? Is for you to stay with me if I don't have all of you. If your not in love with me, then it's not fair to any of us for you to stay with me."