Side Business Ch. 04

Monday night was upon us before long and Jill said she'd put the kids down and that I should talk with Ben and to let her know when it was time to come down. We hadn't heard from Ben since he left Sunday morning so we figured he would still report for work Monday night as usual. Only time would tell if he would indeed show up and how awkward things might be moving forward. We all had a lot invested in the business at this point so I was certainly crossing my fingers that the time and money put towards that would not be for naught.

Ben arrived right on time as I saw the lights of his car pull in the driveway. I wasn't sure what to expect from our conversation but assumed it would be civil at the minimum.

As Ben knocked on the door I opened up and welcomed him in. I figured there was no reason to beat around the bush so decided to get right to it.

"Jill thinks the two of us should talk before she comes down to join us," I started. "So why don't we head down to the basement."

Ben just nodded and made his way down and I followed behind. Ben settled in his normal swivel chair over by the desk where he worked his magic on the computer each night he was here. I sat across on the couch and faced him and began the conversation.

"Obviously a lot has taken place since we were all last down here," I said. "And Jill and I have talked about it and we both felt it was important to talk to you to get your thoughts as well. Our arrangement here has been really good for us and for the progress of our business and you are a big part of that but it would be naïve to think there is not a new dynamic for all of us."

"I agree," Ben began. "I wondered all weekend if I would get a call or text saying not to come back. I wondered all weekend if I should come back. And I really hoped I hadn't caused any damage to your relationship, as you both have been nothing but great to me since we first met."

"Well we're glad you did come back," I answered. "Jill and I decided that the only way for us to have that conversation was to have full transparency with each other. It was the only way to understand what happened the other night and to move forward so all I ask from you is the same thing and we can all take it from there."

"I think that makes a lot of sense," replied Ben.

"Certainly a number of factors led to the other night," I said. "And perhaps it was a perfect storm of things that led it to where it ultimately went. I never thought I would be watching my wife do a strip tease for another man let alone end up giving that man a blow job in front of me. But that's what unfolded."

"I kept waiting for Jill to end it," said Ben. "Then I kept waiting for you to end it. And when she kept going and when you didn't stop it then it got to the point where I didn't want it to stop."

"It was kind of an out-of-body experience for me," I admitted. "The whole thing took me by surprise and it was hard to see it for how real it was. I think seeing that Jill was in control the whole time and that you weren't forcing anything made it ok for some reason. The last thing we want you think is that it was your fault or that you should be sorry for anything."

"I can't tell you how relieved I am to hear that," Ben said.

It was obvious that was true and obvious that he wanted to say more but stopped.

"Go ahead," I said. "It's important to say what you feel. We did it a few times on Sunday and it helped so much."

Ben paused for a few before beginning.

"When I met with you two that first night I did it as a favor to a friend," he started. "I had no intention of working with you."

There was a long pause.

"Then I saw Jill," he finished. "She took my breath away. And when she started to talk I was just blown away with everything about her. And I know I am talking about your wife here and that makes it hard to say. I think Jill is amazing and I think you are the luckiest guy in the world."

Ben started to shake a bit as he talked.

"It's ok man," I said. "Trust me. If anyone understands what you think and feel about her it's me. And I do feel lucky. And I don't mind telling you that we both like you. We both think highly of you. And still do."

"I know you didn't set out to share Jill with me in that way," Ben picked back up. "But the fact that you don't hate me after that is enough for me. It was the most amazing night in my entire life. I hope you pinch yourself a lot because that is all I have done the past day and a half."

I had to laugh at that a little bit.

"But I know why I am here," Ben continued. "And as hard as it may be, and as hard as I may be around her, I will stick to business."

"Well let's just see how it goes," I said.

"What do you mean?" Ben asked.

"The genie's out of the bottle Ben," I answered. "You can't just put it back it in."

"I'm not sure I understand what you are saying," Ben replied.

"Look," I started slowly. "You fucked my wife senseless and she loved it. She did not hide that fact from me. She flat out told me she loved it. She did not hold back in saying how great it was."

"Really?" Ben asked. "Jill loved fucking me?"

"Yes," I answered. "She did."

You could see Ben swell with pride and that new knowledge.

"Does that mean...?" he added.

"Well I don't know the answer to that," I answered. "But I do know Jill has no regrets about fucking you."

"And what about you?" Ben asked. "Do you?"

"I actually don't," I said. "I know it sounds weird but you brought something out of her that was obviously hiding or that I didn't know how to bring out and she has seemed to be a really happy woman these past 48 hours so it's hard to regret that. Whether she wants to explore that side of herself any more we'll just have to see."

"Does it bother you knowing how much I like your wife?" Ben asked.

"No," I said.

"Will it bother you if I fuck her again?" he asked.

"Well I don't think so but I guess we'll take it a step at a time and Jill will have a lot to say about what does and does not happen moving forward," I answered.

"I hope this question doesn't offend you," Ben continued. "Jill indicated when she came down that night that she had your permission to be there. Did you send Jill down to get fucked?"

The question caught me off guard a bit.

"Well after what I had witnessed when it was my turn with her I didn't have much of a chance to last long and that left Jill frustrated," I said honestly. "When I came downstairs and noticed you were still here, and, well, obviously had more in you I let Jill know and left it up to her."

"So you decided that once you saw me?" Ben asked.

"Yeah," I said. "I guess so."

"I just want to make sure I understand," Ben said. "So you saw me jerking off my cock and then you went back upstairs and basically sent Jill down to me to get fucked?"

"Well," I stuttered. "I guess that is kind of how it happened."

"Did you come down and watch us?" Ben asked.

I delayed my response as I suddenly felt like a pervert and Ben saved me some slight embarrassment.

"Don't answer," he said. "I saw your reflection in the window when I was fucking Jill from behind and again when she was riding me. I hope you liked what you saw."

"It was erotic," I said sheepishly.

"Ok," responded Ben. "One last question I promise. Do you want me to fuck Jill again?"

"Well that is up to Jill, " I said.

"But I am asking you," replied Ben. "You said full transparency and I will tell you that I definitely want to fuck Jill again. But I want to know from you if you want me to fuck your wife again?"

This suddenly felt like an answer that had a lot of weight behind it but it was also an answer that only had one of two responses.

"Yes" I managed to say.

A smile came to Ben's face as I saw the light on my phone go off indicating a text. It was from Jill and it said, "Are you guys done yet?"

I held up the phone to Ben and said, "Saved by the bell. I'll tell her to come down whenever."

I texted her back and said we were wrapping up and to come down whenever she was ready. Ben and I had been talking almost 30 minutes now and we did have work to do. After all, we had a business to get up and running.

Ben and I did our best to small talk for the next few minutes. It was more than apparent that Ben was pitching quite a tent. I guess hearing that a woman that you have been pining over loves fucking you certainly get's a cocks attention. Ben was still swiveled in my direction when his face basically froze in place.

I turned my head slightly and saw what had his attention. Jill was walking towards us. She was wearing a sheer black teddy and black high heels. Now Ben's face was not the only one frozen and she was looking right at Ben as she strode with confidence across the room. She stopped next to me and looked down at me on the couch.

"We good?" she asked.

I nodded without speaking.

"I figured we were," she said.

Then she strode the few more steps over to Ben who still sat frozen with mouth open. Jill looked down and noticed the tent I had just seen moments earlier.

"I see the conversation between you two must have been quite stimulating," she said as she looked at Ben and then back to me.

She let those words linger for a bit before continuing.

"I'll get the details later but for now I have a few questions," she said turning back to Ben.

"Do you like me Ben?" she asked.

"Yes," he answered.

"How long have you wanted to fuck me?" she asked.

"Since the moment I first saw you," Ben replied.

"Do you jerk off thinking about me Ben?" my wife asked.

"Yes," he replied.

"How often?" she countered.

"Almost every day," he answered.

"Was it everything you thought it would be Ben?" she asked. "Fucking me?"

"No," he answered. "It was more than I ever imagined."

"Do you want to fuck me again Ben?" Jill asked.

"Yes," he said.

"But I am a taken and married woman," she replied.

"I know," Ben responded.

"And you don't care that I am married?" she asked.

"No," he replied.

"Why not?" Jill asked.

"Because you are the sexiest woman I have ever seen or known in my life," Ben responded. "And you loved fucking me too."

This slow dance of questioning was driving me crazy as I watched them stare deep at each other. Jill was still standing tall looking incredible as Ben looked at her lustfully.

"How do you know that?" she asked.

"Because your husband told me you loved fucking me," Ben answered.

"He did?" Jill answered looking over her shoulder at me.

Jill turned and walked towards me and stopped as she got to the edge of the couch.

"Babe, Ben just told me the craziest thing," she started. "He said you told him that I loved fucking him. Is that true?"

I mumbled what was obviously a "Yes".

Jill leaned over further and kissed me on the lips.

"You are right," she said in a sultry voice as she lifted the back of her teddy so her bare ass was now facing Ben only feet away.

"And this time I want to look at you as Ben fucks me so you truly can see how much I love it," she finished.

With that she looked over her shoulder at Ben who had not moved.

"Do you need an invitation?" she asked him.

With that Jill looked back to me and grabbed my hands and leaned in to kiss me as I saw Ben shedding his clothes in record time out of the corner of my eye. Our kiss continued until Jill broke free with an "Ohhhhhhhh Godddddd."

I looked up and saw that Ben was buried deep inside Jill and had his hands firmly on her waist as he started to thrust into her. She was so wet that even his size went straight in with no issue. Jill looked up at me and her eyes were wide and her mouth was open and she gripped my hands tighter as Ben started to fuck her like he would never get another chance.

I concentrated on Jill's face, as she seemed to roll through a quick orgasm before coming to again.

"That's it Ben," she said. "God you feel so good. Don't stop."

Ben had no intention of stopping that is for sure.

"Pull out your cock baby," she told me. "I want to jerk you."

I shuffled about a bit until I got my pants down and my cock was already erect. My wife grabbed hold of it and the momentum from Ben's fucking seemed to be what was moving her hand as much as anything.

"He is so deep baby," she said. "He is hitting a spot I didn't even know I had. Tell him not to stop."

I looked up at Ben but he again saved me a bit of embarrassment.

"Don't worry man," he said. "I am not going to stop fucking your wife."

Jill let go of my cock and straightened out her body so that she pressed her back against Ben and she reached back and took hold of him from the side.

"Keep jerking baby," she said. "I want you to enjoy seeing me like this."

And I did keep jerking, trying not to come too fast. I watched as Jill leaned her head back towards Ben as far as she could.

"Kiss me," she said.

Ben leaned down and started to kiss Jill with passion as he continued to piston his cock deep into her pussy. I could see Jill's chest start to heave and get red, a sure sign a huge orgasm was on its way. And sure enough a handful of thrusts later and Jill's body was wracked with a knee-quivering orgasm that seemed to never end. Ben never broke his stride, fucking her all the way through each level of her orgasm.

When she came back to earth she puts her hands back on the edge of the couch and as I stared at her beautiful breasts moving back and forth like a pendulum she looked down to me still stroking my cock.

"Baby," she paused. "I love fucking Ben."

And with that I shot huge spurts of cum across my chest and stomach and my wife smiled and blew a kiss to me. I thought I was going to pass out I came so hard.

Jill broke free from Ben enough to turn around and face him. She wrapped her arms around his neck and started to kiss him again. Then she broke the kiss with her arms still tight around his neck.

"You are unbelievable Ben," she said as he smiled at her like the proudest peacock in the world.

"I want you to have what you didn't get last time," Jill continued.

"Really?" he asked.

"Yes," she said with some tenderness. "I want you to be the first."

"I love knowing I will be your first," Ben said. "You have the most amazing ass I've ever laid eyes on. I will make it special.

"I know you will," replied Jill.

Jill turned and looked at me. She had told me on Sunday that Ben wanted to fuck her ass and that she wanted him to so this was not a surprise.

"Are you ok with this?" she asked me looking for assurance.

I just nodded and she turned her attention back to Ben.

"I don't want to do this in the basement," she said.

It now dawned on me what she really meant by asking if I was ok with this. She took hold of Ben's cock with one hand and started stroking it. I could see her wedding ring glistening with her cum that had coated Ben's cock just moments earlier. She looked up at Ben wantonly.

"Ben," she said softly. "Take me to our bedroom."

Ben was no longer waiting on invitations whatsoever. He lifted Jill up and cradled her and I watched as he started to carry her across the room as they kissed. I saw his naked ass carry off my wife out of the room and up the flights of stairs. I followed quickly behind.

I arrived to the room just a few steps behind and the room had candles lit, the lights down low and music playing. Jill had anticipated this moment and how she wanted it to happen. She was treating this moment of her anal virginity as one might treat their first time altogether.

Ben laid her down softly on the edge of the bed and he looked around and seemed to understand that this was a significant moment for Jill and perhaps for him as well.

"Do you want me to get on all fours?" Jill asked.

Ben just shook his head and scooted Jill up the bed even further and looked at her.

"What is it?" she asked.

"I..." he paused.

"You can say it," Jill encouraged.

"You look so beautiful," Ben said. "I..."

"Tell me Ben," she said.

"I want to make love to you on this bed first," he finally said.

I felt like I could almost hear Jill's heart melt a bit. I have to imagine that for Ben as much as he was enjoying the night and the moment there was a part of him that still thought it would never happen again and he better take advantage. And for Jill, who I knew was exploring this new role and her newfound sexuality, Ben had just cracked a piece of that. At least that was my interpretation.

"Can I?" he asked.

Jill opened her legs invitingly to Ben and she put her hands on him.

"Yes," she said.

Jill reached down and grabbed Ben's cock and brought it to her still wet opening. She stroked it across her clit a few times and then put Ben's cockhead inside her and let go, cueing Ben that he had the green light.

I had watched Ben fuck Jill on Saturday night and into Sunday morning and earlier this night as one would fuck someone that they just wanted to pound away at. But right now Ben was slow, steady and as deep as he could be and he and Jill stayed tight together in a missionary position throughout. Over the next 15 minutes or so Jill had at least two orgasms that I could make out when Ben pulled out and flipped Jill over on all fours facing my direction.

Ben got behind her and wasted no time with his tongue and fingers devouring Jill's ass and getting it ready for his engorged cock. He spent several minutes, all of which Jill seemed to enjoy based on her reactions and sounds. Then I saw Ben rise up from behind Jill and position himself directly behind her.

"I'll go slow," he said to reassure her.

Jill nodded as she looked at me. With that her eyes began to open as Ben started his way into her ass. The next few minutes seemed like a blur as I watched attentively as Ben inched his way in a little bit at a time.

Hearing Ben talk to Jill broke my trance-like state.

"How do you feel?" he asked her.

"Amazing," she said. "It feels fucking amazing."

"You have all of me Jill," Ben said.

"You feel so good Ben," she said. "I'm ready."

Ben slowly started to pick up the pace. Ben's pace was never fast but it was steady and it looked to me like he was in heaven on earth.

"How do I feel Ben?" Jill asked.

"Incredible," he said. "I don't think I can last."

I could only imagine how tight the grip was of my wife's ass on Ben's cock so it did not surprise me that he was experiencing a sensory overload. Jill again looked amazing on the receiving end of being fucked. Her beauty was always evident to me but this was something different I was seeing in her these last couple days. This was a woman unleashed, experiencing life in a new and confident way. If you had told me 72 hours ago I would be watching my wife get her ass fucked on our bed by someone not named me I would have thought you crazy.

But here she was with a looming orgasm about to take over her world, as Ben seemed destined to join her in that bliss. And sure enough they both arrived at a nearly identical time with Jill's orgasm overpowering her and sending Ben over the top and he thrust forward powerfully and undoubtedly emptying a massive amount of cum into Jill's ass.

It took them both a bit of time to recover from the moment as I looked on quietly. Jill finally rolled off the bed.

"You two go put your clothes on and I'll meet you downstairs," she said.

Ben and I made our way back to the basement and neither of us said a word until we were joined by Jill about five minutes later.

"So I knew there was no way we were going to get any work done tonight so why even bother," she started. "You owe us a night of work later Ben by the way. As for what is going on here I need to make a few things really clear before this goes any further."

In case there was any question my wife was about to set some rules.

"Ben," she started again. "Jack is my husband. I love him. I feel things for him that no man will ever provide. I love him even more than I thought I could after these last couple days as he lets me explore this side of me that I didn't even know I was capable of. And if he ever decides it is too much then it is over. Do you understand?"