Jay's Sex Club Adventures Ch. 02

I pulled out finally, my cock had gone limp. I removed the condom and tossed it before lying down beside her. Holly snuggled closer to me and we simply stayed like that for a few minutes, our sweaty bodies pressed together.

"That was a lot of fun," she was finally able to say.

"Yeah... I'm so fucking tired now," I laughed and so did she. We finally got up and started to dress, and I looked at the clock on my phone... it was almost 1:00 in the morning and I had missed three calls from Rob and one from Annie.

"Shit," I swore under my breath.

"Everything okay?" Holly asked.

"Yeah, I just didn't realize Rob was trying to call me. I hope he didn't leave without me... I didn't bring my car tonight and I'm screwed if he did leave."

"Well, let's hurry up and go find him."

We left the basement and thankfully, after some searching, I found Rob and Annie outside smoking a cigarette. Rob was drunk, but Annie was sober enough to drive in his place. I gave Holly a hug and a kiss, said goodbye and the three of us left, getting into Rob's car with Annie driving me home.

The next day was Sunday. I woke early, around 9:30 am or so and got up to start doing my wash and some other Sunday activities. I took a shower, packed my laundry bag and made my way out to the Laundromat.

The whole day that I spent there, I spent it thinking about everything I had done the last two days, I'd had a lot of fun with Lisa on Friday, but I almost felt like I had even more fun with Holly last night. Not that I liked Holly more than Lisa, or Lisa more than Holly, truth be told, I could have probably had almost as much fun with Lisa if I had said yes when she asked me to suck her cock.

I told her I would think about it and maybe do it the next time, which would have been last night, but her car broke down and so I wound up doing it with Holly instead. Although, I had never originally intended on sucking her cock... I just planned to have sex with her. But stuff happens sometimes.

I got home from the Laundromat around 7:30, put everything away and made dinner before going to bed around 10:30 that night. I had work in the morning and I was really hoping that this week would go by as fast as possible. Then I could get back to The Raven on Friday and hang out with both girls this time.

I got my wish, the week went by fast. By Thursday night though, I realized I had not spoken with Lisa since Saturday when she called to tell me she could not make it to the club. I decided to give her a call Thursday night and ask her if she wanted to come over, spend some time together and have dinner. I called and she picked up, sounding happy to hear from me.

"I was wondering if you would want to come have dinner at my place."

"Tonight? I would love to, but I have work in the morning. I will be at the club tomorrow night for sure though, my car is fixed, see you there?"

I hung up feeling a bit disappointed, and went to bed early, I just wanted tomorrow night to get here as fast as it possibly could. Friday morning I woke up and took a shower, got dressed for work and was out the door by 8 am.

Work flew by, lunch break came before I knew it, and when I sat down and checked my phone I saw that I had a voicemail from Lisa. I punched in my voicemail password and put the phone to my ear.

"So you little cock sucker... I heard all about what you and Holly did last Saturday. Call me back when you get this, okay?"

"Shit," I thought nervously, "Is she pissed off at me? I thought she was okay with me hooking up with Holly, she said it herself that it was okay."

I thought that maybe I had misunderstood her or something... I only hoped she was not too angry with me, as I did not want to lose her friendship. I dialed her number and the phone rang three times before the click of someone picking up signaled that I was about to find out for sure if she was pissed.

"Hello?"

"L-Lisa... its Jay,"

"Hey there you," she said. She definitely did not sound too pissed off, but I was still a little paranoid because of the voice mail she had left me, "How's it going?"

"It's... okay. Listen, I got your voice mail... I'm really sorry."

"Sorry? No, its okay, I'm not angry with you," Lisa said.

I let out a heavy sigh of relief and leaned back in the chair I was sitting in. I was definitely very happy to hear that she was not pissed off at me as I had assumed she might be, "That's great, because I was pretty worried you were."

"Of course not Jay, I told you it was okay for you to have some fun. I just didn't expect you to be willing to do anything like that with her."

"Yeah...it was kind of a spur of the moment decision," I said laughing nervously.

It was not a lie, I had not gone into the basement with the intention of sucking Holly's cock. Sure, I had enjoyed it, but it was not planned.

"Did you have fun?"

"Well... yeah, it was cool, I liked it."

"Good... because tonight, I want you to show me what Holly taught you, got it?"

I laughed and quietly hinted that it was okay with me, and a few minutes later we hung up so that I could return to work. I was happy to know I was off the hook, that Lisa was not mad at me, as I imagined she was. The only thing she expected was for me to do for her what I had done for Holly.

In spite of the fact that I had already done it once, and even enjoyed it to a point, I was still nervous about doing it again and this time with Lisa. It was only fair though, I had promised her I would think about it and wound up doing it the first time with Holly when it should have been Lisa who got the first chance.

The rest of the workday went by quickly, and before I knew it, and the day was over with, thankfully. I clocked out and made my way home to get ready for what I was sure was going to be another exciting and fun night at The Raven.

When I arrived home, I stripped out of my work clothes and went straight for the shower making sure to clean up real good. I brushed my teeth, put on some fresh clothes and sprayed some cologne to add to the style. When it was all said and done' I waited for Rob to show up with Annie.

When they finally got to the apartment, I met them outside and we decided to go to a restaurant and get something to eat before heading to The Raven.

An hour and a half later and we had parked the car up the street from the club like usual and were making our way towards the front entrance. Rob and Annie were all over each other like they normally seemed to be, and I was very excited to get inside and meet with Lisa.

I found her at the front door with Holly and Jen smoking a cigarette. She smiled and waved at me as I got closer to the door with Rob and his girl, and she put out her cigarette and met me halfway with a big hug and a kiss on the lips.

"I'm glad to see you, I missed you," she said giggling.

"Likewise," I replied. Holly looked over at me and winked, and I blushed. Lisa laughed and gave me a nudge towards Holly who proceeded to pull me into her arms and give me a hug as well.

"I heard you were convinced Lisa was going to be pissed at you?"

"Yeah... I guess I was wrong though, what a relief."

"Lisa rarely ever gets mad," Holly said, laughing,

"And besides, we've always enjoyed sharing our men equally so of course she wouldn't mind."

"No, I didn't mind," Lisa chimed in innocently. "I just want to see if you're as good at sucking dick as Holly claims you are."

I blushed as she took me by the hand and led me into the club. We sat down at the bar and ordered a couple of drinks. No rush, Lisa said. It was only 8:30 at night so it was easy to sit back and have a few drinks before heading off to the basement to have fun together.

"So how've you been," she asked, completely skipping over the topic we had been on just a few short minutes ago. That made me feel a little less anxious to be talking about something unrelated to what we were going to be doing in an hour or two.

"I've been okay, I just really missed you. I'm glad you made it tonight."

"You're so sweet," she teased me.

"You know it occurred to me recently, that I don't know much about you. So, tell me about yourself Lisa."

"About me, what do you want to know?"

I told her to tell me whatever she wanted, and she smiled and started to tell me her life story. Apparently, she had grown up in New Jersey, right across the bridge. When she was a boy, her name was Joseph; she lived her life as a man until she was eighteen years old when she moved out on her own. From there, she started dressing as a woman and eventually started doing it full-time...now at twenty five years old herself, she had been living full-time as a woman for the last seven years, quite happily too.

When she was done explaining, I felt happy to know more about her then just the sexual side. I hoped to get to know some of the other girls as well... I enjoyed being here, but I did not like the idea of just having random sex. I liked to know that these people were my friends as much as they were my sexual partners. And I wanted them to know that I was their friend too.

Eventually though, it came to the point where Lisa wanted to get to the point. She had moved off her bar stool at some point, and was now resting on my lap, flirting with me. That turned into us making out together and she took me by the hand and guided it down to her leg.

I ran my hand up her smooth leg and under her skirt to find she was wearing no panties, and damn was her cock hard as a rock. I stroked it slowly at first, then a little faster and she moaned biting me on the neck.

"C'mon lover boy," she whispered in my ear. "Show me what Holly taught you."

We made our way into the basement and picked a room and once inside, Lisa pushed me against the wall and crushed my lips with her own. Her tongue slid into my mouth in a passionate French kiss, and I held her close to me. I could feel her cock poking me even through our clothes.

I decided it was time for me to take control, I still was not very good at this, but I was eager to please. I broke the kiss and guided her towards the mattress, where she sat down at the foot of it and I got down on my knees.

Excited, she lifted her skirt and there was her raging hard cock. She leaned back on both hands and watched lustfully as I took her in my hand and started stroking. "Mm," she moaned. "Nice way to start off, I suppose."

"Don't worry, it'll get even better," I assured her.

"I'm sure it will," she said in a seductive voice smirking at me.

That was my cue, I thought, as I leaned in close and started off by giving the head of her shaft a lick. She tasted like strawberry body wash, it was great to know she had cleaned up before coming here, and had even used a type of soap that would taste good. I continued teasing, licking the head of her shaft, before I started licking up and down her shaft and over her balls.

I started focusing on her balls, licking them each one at a time, before taking one in my mouth and sucking on it. Lisa moaned louder this time, and as I sucked on her one ball I stroked her cock as well. I released her left ball, and then moved to her right one sucking on that one for a few moments.

"Oh god," she muttered, "So far I'm not disappointed Jay... but please, get to the damn point already," she laughed.

I released her right ball and moved back up a little to the tip of her shaft before finally sealing my lips around her. She gasped as I did, and I took her as far down my throat as I could before I started to gag.

I pulled back some, then moved back down a little further choking once again. I kept pulling back and moving back down every few seconds and each time I managed to take more of her to the back of my throat.

Soon enough, I had all seven inches of her raging hard-on in my mouth, deep throating her with slight difficulty. Every couple of seconds I would choke or gag, but I was certainly beginning to get the hang of this I thought.

Lisa seemed very impressed at my efforts as well. She was now running her hand through my hair, her head leaned back, her other hand pulling at the silk sheets and groaning as I continued sucking her cock as best I could. She tightened her grip on my hair eventually, and began moving my head up and down on her shaft as though she were guiding me. The realization that she was taking control of the situation seemed to turn me on more.

"That's good Jay, I like that, just like that baby."

Hearing her approval, I began moving up and down faster, and also added a hand to cup and massage her balls for a few moments. I moved that same hand up her belly to her breasts and began to massage her left breast, pinching and squeezing her nipple. Her breathing started to get heavier and she started thrusting her hips upwards, pushing her cock in and out of my mouth now.

"Fuck baby, keep that up and I'm going to cum real soon,"

That's exactly what I wanted to happen, and so I did indeed keep it up and as I did I noticed her reaction increasing. She was moaning louder now, her breathing heavier and faster and pulling on my hair.

"Fuck, yeah, oh god I'm going to cum," she warned me, "Pull off, I'm going to cum!"

I did not back off though, if she was anything like me I was pretty sure she would enjoy the idea of being able to cum in my mouth. So I kept my lips firmly wrapped around her took and within moments I felt her entire body begin to shudder.

"Oh shit, here it comes," she cried out in pleasure.

I felt her erection begin to pulsate, and then I felt the hot sticky cum flowing into my mouth.

This was the second time I had sucked cock, but it was the first I had actually tasted cum. When I went down on Holly, we had stopped before she reached her orgasm and so I had not had that experience at all until just now.

To be honest though, there was not much to it. It did not have any notable flavor that I found enjoyable. But it was not disgusting either, nevertheless, I enjoyed the idea that I had allowed her to cum in my mouth, and I swallowed every drop to further satisfy her.

"Oh wow," she sighed feeling relieved, then teased me as I licked the head clean, "That was hot, and you swallowed it all too, such a good boy!"

I pulled away and she pulled me up to eye level kissing me on the lips, sliding her tongue into my mouth.

"Want to fuck me," she asked seductively.

"That shouldn't even be a question, of course I'd love to."

I flipped her over onto her back and she cried out in shock, and then started laughing. I fumbled with my belt and zipper, sliding out of my jeans and boxers. I did not bother to remove my shirt right away, and likewise, Lisa remained in her clothing simply lifting her skirt further since she had no panties.

I lifted her legs and moved between them, kissing her passionately and probing her asshole with my raging hard cock.

We both moaned, and I pushed forward, my dick slipping into her hole, which surprisingly was not very tight. She must have been playing with herself before she came here tonight in an effort to loosen herself up in advance.

I still swore though that her ass was tighter than any pussy I had ever fucked, and it felt just as great as last time and just as great as Holly's ass felt.

"Oh god, fuck me," she cried out. I started pounding her ass, legs wrapped around my waist, the bed shaking underneath of us and the both of us were moaning in pleasure and gasping for air

She moved both hands up under my t-shirt over my back, racking my skin with her nails and biting my neck. In and out of her ass I thrust, building myself ever closer to the inevitable orgasm I wanted so badly. She reached down between us and started stroking her own dick as I fucked her, and soon we were both right on the edge.

"Are you going to cum," she asked, breathing heavy.

"Oh shit, I'm almost there."

"Pull out," she said desperately, "I want you to cum in my mouth."

I wanted to finish in her asshole, but I could tell she really wanted it and so I figured I would give her what she wanted. I withdrew from her ass and moved up some so that I was right up in her face. I started stroking my cock, but she slapped my hand away and instead pulled me to her wrapping her lips around me. I bit my lip, moaning, and then I felt something I had not quite expected to feel.

I felt her finger probing my asshole; and then I felt it slip into me. It was not painful, a little strange at first but once she found that spot, the right spot; the prostate gland...there was no turning back for me.

Keeping my dick in her warm wet mouth, and her finger pressed firmly against my prostate, Lisa had me right where she wanted me. I felt my body tense up, my dick begin to swell, and finally I burst inside of her mouth. Huge globs of semen blew from the tip of my member shooting right down her throat and I sighed as I felt the tension leaving my body.

After she had swallowed it all, Lisa released my cock from my mouth and I felt myself begin to go limp. My whole body loosened up, including my backside and I felt her finger slip a little deeper into me.

"You like that baby?"

"Mm... it's not bad," I replied truthfully. It was not the greatest feeling in the world either, but I could not deny that it did feel good. It had certainly added to the intensive orgasm I had just experienced, which would have been great even without stimulating my prostate, but I was not complaining.

She continued rubbing that spot for a few moments and then started moving her finger in and out of me. I moaned softly and she flipped me over onto my back, I snapped out of the post-orgasm state I was in and realized the awkward position that she had me in now. I was in the same position she had been in just a few minutes ago while I was fucking her, and on top of that she still had her finger in my ass.

"H-Hold on," I said.

"Shh," she pressed her other hand to my lips. "It's okay... I won't take it that far if you don't want me to. I'm just giving you a little massage is all,"

I trusted her enough to know she was serious when she said she would not go too far unless I wanted it to go that far. There was nothing wrong with what she was doing right now as long as it stayed where it was.

Plenty of guys out there enjoyed prostate massages, I had read up on it a few times in the past. It did not mean you were gay or bisexual even, it was just another way of getting off and a lot of' men felt like it was worth it too.

Hell, I had had a girl a few years ago offer to do it for me, a genetic girl. I had been too much of a chicken shit at the time to approve it, but now I was wondering why I had not gone through with her offer, because this did feel pretty good.

I noticed my cock was hard again, sticking straight up at full attention as she continued to massage my inner spot.

With her other hand she started rubbing my nipples for a few moments before replacing her hand with her lips. Sucking, licking and biting my nipples, she had me writhing underneath of her in pleasure as pre-cum began to leak from the tip of my cock.

As I felt myself building up to yet another and possibly stronger orgasm, I realized that Lisa was not even touching my dick; she was simply focusing on the prostate massage and using her lips to lick my nipples and now my neck as well. Then it hit me with overwhelming force as she sped up her hand motions and started sucking on the left side of my neck hard.

My whole body locked up and I gasped for air as a hot burning sensation shot through my cock and I spewed another hot load from the edge of my member, this time all over my chest. I had certainly come that much in the past, but never so hard; I let off at least six or seven straight shots.

They went high up into the air to before falling back down onto my chest. As she continued biting and sucking my neck, I heard Lisa giggle' before backing away from me.