Our Friend Jack Pt. 02

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Then his message came through. Who is this?

Oh fuck! I felt a flush tear through my body and my palms immediately became wet with sweat. My heart pounded in my ears. What the fuck do I do now? I could ignore it and shut down my computer and try to go to sleep. I was sure that there was no way he could find out who sent him that message. At least I was pretty sure.

I just sat there and did nothing.

Hello? I don't know who you are.

My mind went back to earlier that evening and pictured Marie in the hot tub bringing herself to orgasm because of the scene that I was describing to her. Namely making my friend cum right in front of me. She wanted to do it and so did I.

My hands were shaking as I began typing.

Hi. It's me. Don't use my name once you figure out who this is.

It was a long minute before he responded.

Give me a hint.

He wanted a fucking hint!

You really like my hot tub!

What the fuck are you doing up so late? I would guess that you are jerking off but you need both hands to type.

He just can't stop being Jack.

Promise me that you will delete this conversation after. I don't want any evidence of it to hang around.

I could almost hear him laughing.

Are you a spy or something? Do you need to hide a body? You know I am ok with that right?

Please just promise!!

I figured adding exclamation marks would really underscore the importance of my request.

Sure. No problem. I promise I will delete this conversation.

One thing I knew about Jack. He always kept his promises.

I still had one more chance to change my mind. Once Jack had even an inkling of what I was proposing he would be like a dog on a bone.

I have something to talk to you about.

His response came almost immediately.

I figured something was up. It's way past your bedtime.

I smiled to myself. The tone of his messages was going to drastically change once he understood my intentions and this strangely gave me a sense of control.

We had a very interesting night.

There was no need to mention names. He knew who I was referring to.

Are you going to tell me why it was interesting or will I have to guess?

As much as I wanted to drag this out I was also goddamn horny. I wanted to talk about sex. I wanted to see if this was really going to happen.

Let's just say that we had fun in the hot tub and we sort of talked about things.

I didn't have to wait long for him to reply.

Now you have my attention. What sort of fun did you have and what did you talk about????

I figured that it was reasonably safe to write anything now.

We talked about some interesting scenarios and what would happen if we ever invited others into the hot tub with us.

My cock started to stir in anticipation of where this conversation was heading.

Ok. I'm liking this so far.

I was imagining him sitting at his computer stroking himself which only made me more excited.

I took a deep breath and continued typing.

There may be a possibility that she might and I mean might be interested in doing some things.

I didn't want to write too much too quickly but it seemed that, with every key stroke, my cock got harder and the harder I got the bolder I became.

While I waited for him to respond I took off my boxers and teased myself by gently running my finger up and down the length of the underside of my cock. A small drop of precum appeared at the slit in my cockhead and I used my finger to massage it into the sensitive skin around it. I imagined Jack doing this to me and Marie sitting beside us watching.

I had to quickly back off as the unmistakeable signs of release started in my balls. I didn't want to finish before I told Jack everything.

Jack's messaged popped up on my screen bringing me back to reality.

Just to make sure I am getting this right. We are talking about sex right? With your wife right? When you say doing things you mean sex????

I wanted to be cautious and take this conversation slow but I also wanted to tell him that yes I was talking about sex and not just with my wife. I had to resist the urge to stroke my cock to completion right there.

I took another deep breath to calm myself.

I'm not entirely sure what I mean actually. She is interested in things and so am I. It does involve you but I don't know where to go from here. She wants to see and experience things but she is scared and so am I. I hope you know what I mean?

I felt a little ridiculous sitting in my chair naked with my dick sticking straight up and me typing away like this was all very normal.

I went on not waiting for him to respond.

I don't want this to make things awkward between us but I'm so fucking horny all the time thinking about it and I feel I need to step outside my comfort zone.

I was pretty sure that it was my cock that typed that sentence because I instantly regretted hitting send as soon as I did.

His reply was quick and immediate.

Fucking cool. Just to let you know I am hard as a rock right now.

Here we go. My mouth was dry and my heart was pounding in my chest. I was only partially certain that what I was typing was actually legible.

Me too!!

Fuck! Why did I type that? Why did I send that? Was I prepared to actually do this? I didn't like losing control of things and this had the real potential of spiraling out of control very quickly. Still I couldn't stop myself.

What does she want to see?

I knew this question was coming. I sat for a moment staring at my screen not knowing how to respond. Luckily my cock knew what to say.

You know how men love to watch two women get it on?

Of course. What's not to love about it??

I held my breath as I typed.

She's the same.

She wants to watch two women have sex?????

I guess I shouldn't have expected him to get it right away.

Maybe but that's not what I mean.

It took him a few moments to respond.

Oh. I see. Ok.

What did he mean by "Ok"? Was he just telling me he understood or was he Ok with it?

Before I could type anything else he messaged me again.

Is this something that might interest you??

I couldn't answer right away. I was stroking my cock and bringing myself close to the edge. My hand was slick with my precum now and I felt light headed. It took every ounce of my waning self-discipline to redirect my attention back to my keyboard.

Maybe. I think so. The idea really turns her on.

Does it turn you on?

He knew how to read between the lines.

I had to be honest with him.

Let's just say that at the moment I am probably 3 or 4 strokes from making a mess all over my computer!!

Nice!! Me too. Is there anything in particular that she wants to see?

I didn't want to get too carried away so I kept it simple.

She's not interested in kissing or romance stuff. Neither am I. She wants to see you use your hand on me.

She wants to watch me jerk you off???

Yes

Would this happen in your hot tub?

Yes.

I couldn't tell if I was scared or excited by the fact that we were actually discussing this happening.

Would she be in the hot tub with us???

I had to think about this one for a bit. As much as I would love for her to be right there beside us I thought that she would be more comfortable watching from in the house.

I don't think so. She would be watching from inside. It would be up to her how much she wanted to get involved. Another important thing is that if she wanted to cancel it at the last minute she could. No questions asked.

I waited for a few minutes and there was no response. I figured he was either typing a long response or jerking off. I was pretty sure it was the latter. My cock was hot to the touch and I squeezed it lightly at the root. I was so very close to cumming.

Let's do it.

Those simple words typed out by Jack sent a shockwave of fear through my body. Up until this point we were just having fun. It wasn't real. We were both horny and didn't really have to take it seriously. I sat back in my chair and stared at my keyboard; willing it to type something that would get me out of this.

It just stared back at me as if to say that I got myself into this mess. I knew that I didn't want to back out now. I wanted to see Jack's hand wrapped around me and stroking me to a mind blowing orgasm. I wanted to be able to look up and see Marie watching from the window. I wanted to see her make herself cum at the same time.

I tightened my grip around my cock and started slowly stroking. With my left hand I typed OK.

Jack got back to me right away.

About to cum

It was almost too much of an effort to answer.

Me too

I felt myself thickening and my climax overtook me. The pent up tension deep within my core immediately released and surged up from under my scrotum to spread throughout my body. With my free hand I pressed on my taint adding to the intense pleasure causing me to cry out involuntarily.

I held off as long as possible to heighten the feeling of euphoria but then my body reflexively shuddered and I shot seemingly endless streams of cum on to my stomach and chest. Through the palm of my hand I could feel the pulse of my ejaculate surging through my cock and kept stroking well after I could no longer coax any more out. After two incredible orgasms in one evening I had nothing more to give.

Even after the spasms subsided I was shaking from the intensity of my orgasm. I kept my eyes closed waiting for my heart beat to slow down to something near normal.

Looking up at my screen I saw that there was a message from Jack.

Did you finish?

Yeah

Was there a lot?

I glanced down at my chest.

Oh yeah

Did you hit 4 feet this time?

I just smiled to myself.

I needed to clean up and go to bed.

Let's talk later

I had some thinking to do.

Since I was up so late I had planned on sleeping in but found myself awake and restless as the sun starting peeking in our bedroom window. I looked over at Marie. The features in her face were so relaxed as she lay there still in a deep sleep. The natural beauty of her skin highlighted the soft, fullness of her lips. Those same lips that I imagined pleasuring my best friend only a few hours before.

I felt that familiar reviving of desire so I forced myself to get out of bed rather than wake Marie. Truthfully my balls ached a bit and I figured I needed to give them a much needed rest.

I made my way to my computer fooling myself into thinking that I was going to do some work. After a few minutes I gave up on that plan and opened up my e-mail. I had forgotten to delete the conversation with Jack and, as I started to reread it, wondered if I might look at it differently in the light of day and without sporting a hardon. I didn't.

The whole idea appealed to me even more.

After deleting the chat I sat back to think. As much as I wanted Suzanne there I thought that there would be less pressure on Marie if it were just Jack for what I hoped was only the first time. If she didn't feel comfortable then she could just back out and nothing would happen. I knew that Suzanne worked nights every second weekend and so figured that the following weekend would work the best.

I also had to come up with some sort of signal so that I could tell if she didn't want things to progress further. The first idea that came to mind was that, if she left the ceiling light on in the guest room, I would take it as a sign that she didn't want anything to happen, period.

I quickly typed a quick message to Jack asking him if he wanted to come over to watch a game on Friday night and hit send before I could change my mind. I wanted to keep it light and, besides, he would be able to figure things out.

I checked for a reply later that morning and, sure enough, Jack got back to me saying that he would be happy to come over. I was glad that he didn't say any more than that not knowing if anything was actually going to happen. Somehow I still needed to let Marie know about it without freaking her out.

It was Wednesday before I gathered up enough courage to let her know. I decided that I would send her an e-mail so that she could be alone when she read it and, more importantly, I wouldn't make a fool of myself trying to sound casual when I told her.

It took me about an hour to finally come up with a message that sounded nonchalant but also got the point across.

Jack will be coming over to watch the game on Friday night and maybe enjoy the hot tub. If you want nothing to happen leave the guest room ceiling light on. I will absolutely understand and respect your decision.

After having read and reread it at least 20 times I decided it didn't sound too pushy. It took me another hour to hit send.

I purposely sent it to her work e-mail so that it would be Thursday morning before she would get it. By mid-morning I got a reply. It simply read Ok.

If Marie was concerned or anxious about my plan she didn't show it when she got home that night or the next day when she left for work. In fact it was almost as if she hadn't read my e-mail at all. In sharp contrast I was a bit of a mess, at least on the inside. Outwardly I was holding it together pretty well. Most of the day Friday was spent watching the clock and second guessing myself.

We were expecting low temperatures and rain in the evening so I lit a fire when I got home and prepared supper. Marie was still not showing any indication that this evening was going to be any different than others which actually helped me relax a bit.

It wasn't until just before Jack was supposed to show up that she told me that she was going upstairs to read. Normally she would have curled up in front of the fire and settled in for the evening. I had worried about how things were going to go between them when he did finally show and this helped alleviate that concern.

Just after 7 I heard the doorbell ring which surprised me. Jack would have normally just walked in. When I opened the door he was standing there and he seemed different. My first thought was that looked nervous. Maybe even a little scared.

I stepped back from the doorway to let him in but he didn't move. Instead he just stood there. It had just started to rain and he was starting to get soaked.

"Aren't you going to come in?" I asked.

He nodded and walked by me, stopped a few feet from the door, and quickly scanned the room.

"She's upstairs reading," I told him in response to the puzzled look on his face, "she's not into hockey."

He seemed to immediately relax. "Suzanne is the same. She actually can't stand watching it."

I went to the fridge to get him a beer. "Are you hungry? Have you had supper?" I called out from the kitchen. He was warming himself by the fire and seemed to be mesmerized by the flames.

"Jack?"

"What? Sorry?" He slowly looked up from the fireplace.

I pointed at the fridge. "Do you want something to eat?"

"No. I'm good," He replied distractedly.

I turned on the TV and sat on the couch motioning for him to sit down. He glanced towards our stairway a few times before he joined me.

We watched the game in silence for a few minutes. This was not normal for Jack. By now he should be offering up all kinds of innuendos and insults. This is especially true when he watches hockey.

"Are you ok?" I was getting a little concerned.

"I'm fine." He didn't sound convincing.

"I got something for you." I stood up quickly and went to the kitchen.

When I came back I handed him a small container.

"It has been years since I made these and I thought I would give them a try again."

He looked up at me. "Are these what I think they are?"

"Oh yeah." I smiled.

Jack took a brownie out of the container and tasted it.

"Not bad," he said. Popping the rest of it into his mouth he reached for another.

"You might want to take it easy with those. I don't know how strong they are." I cautioned him.

He just smiled at me and finished off the second one. I took one for myself and sat down.

When I decided to make the brownies they were supposed to be for me. To help me relax. As it turned out it seemed they might have been for both of us.

We sat there for a while talking about the game and doing our best to make this seem like a typical Friday night. Jack seemed to be more at ease and I began feeling relaxed as the brownie started to take effect. Any apprehension about what I was planning was quickly dissolving away.

Without saying a word I got up off the couch and went over to the patio door to look outside. I had a surreal sense of confidence come over me and decided it was now or never. I grabbed a few towels and threw one at Jack.

"Hot tub time my friend." I wanted to take control of this situation. I needed to.

Opening the door I stepped out into the cold night air, uncovered the tub and turned on the underwater light. I glanced up at the guest room window and saw that the room was dark. I started shivering but couldn't tell if it was from the cold or nerves.

I didn't waste time getting undressed and quickly got in. Sitting with my back to the door I reclined against the seat and closed my eyes. The heat from the swirling water started calming my nerves immediately.

I heard the patio door open and close and soon sensed the water rise as Jack got in.

My mind wandered back to the previous Friday to the scene that I painted for Marie; that of her stroking Jack's cock while I watched. I pictured her cupping his balls gently while massaging the underside of his cockhead with her thumb. Something that would have been unthinkable in the past was, at that moment, what I wanted to experience the most.

Opening my eyes I saw that he was staring at me and repositioned myself so that Jack could easily see that I was semi-erect. I wanted to expose myself completely to him and was feeling a sense of power that was foreign to me.

I glanced surreptitiously toward the second floor and was relieved to see that the room was still dark. It was then that I noticed a slight movement in the window. It was too dark to see any details but there was no doubt in my mind that Marie was watching us. From her vantage point she would clearly be able to see that I was aroused.

I wanted to put on a great show just for her.

My high was just starting to really kick in and it felt like I could feel every jet massage me. I reached under the water and grabbed my cock, giving it a squeeze. It felt so good in my hand.

"Do you want me to show you how much I love my hot tub?" My voice sounded detached.

Jack nodded and smiled. He looked like he was feeling the full effects of his double dose of brownies.

I stood up slowly and sat on the edge of the tub exposing myself completely. It was just starting to rain and the cold droplets stung my hot skin. I couldn't imagine ever having being more aroused. Knowing that my wife was watching was almost more than I could handle.

I leaned back so that my cock was lying flat against my stomach. Jack was no longer smiling and instead was staring intently at what I was doing. I gave myself a few slow jerks. My balls, the skin relaxed from the hot water, rose and fell with each pull.

"Are you going to show me how much you love it too?" My voice, hoarse and low, belied my inner turmoil. My heart felt like it was going to explode from my chest. I wanted him to replace his hand with mine and finish me off then and there but I didn't want this to end yet. Besides, Marie needed her show.