Side Business Ch. 05

I did housework, did some work, watched some tv but nothing seemed to get my mind off Ben and Jill. So I did the only thing I could enjoy. I looked at her picture on my phone and started jerking off. I was going back and forth between the two, imagining their evening when I got another text, this time from Jill.

"Having fun but had too many drinks to come home tonight," read the text.

"Is everything going well for Ben?" I returned.

"Yes," she replied. "His star is on the rise and I've made sure of it. His co-workers seem to love me too. I'm still charming them."

"And are you having fun?" I asked.

There was a little delay before the next text came in.

"You could say that," she replied.

"What does that mean?" I said.

There was another excruciating delay.

"We just fucked again," came the reply.

It was only 10 o'clock and if she was still charming them then how did they already fuck, let alone again.

"How if you are still at the event?"

After another delay came the answer. It was a videotext of the two of them fucking standing up in what looked like a closet. Ben was behind Jill holding the phone with her dress around her waist literally fucking the hell out of her. She was begging him to fuck her harder and deeper and he was obliging.

The video lasted about five minutes and ended with Jill's second orgasm and Ben unloading inside my wife. I don't think that video was originally made for me but rather for their own keepsake but perhaps the alcohol made Jill feel like she could send it.

Either way, the next text came saying that she was putting her phone away to start dancing and that she would talk to me tomorrow.

I came two more times that night watching that video. It was the reminder of what Ben provided that I didn't. Deep and powerful thrusts that lifted Jill off her feet and filled her completely one after the other until her legs got weak in the knees. The last time I came nothing even came out I was so drained but each orgasm felt strong in their own ways. I finally drifted off wondering how the rest of the night and morning was going to turn out.

I was a bit groggy the next morning after a rough sleep and slow to get the kids up and running. My mind was racing wondering when my wife would return and what state she would be in. I told the kids it was too late for her to drive home last night. While my mind wandered over the course of the morning the saving grace was that only one of two things could be happening. They were either sleeping or fucking.

It was about noon when I heard the car pull in. Jill came in the door by the garage and immediately went upstairs not coming through to the family room to even say hello. I thought that was a bit strange but within minutes she was down to give the kids hugs and me one as well. I also noticed that her ring was back on so perhaps going upstairs was nothing more than to do that.

She told me she loved me and looked at me tenderly very aware that I had suffered through a tough night of emotions. She made sure I had noticed that her ring was indeed back on.

"Did you get any sleep?" she asked.

I just shook my head and said, "not much."

She rubbed my face and held on to me while I sat there and started to feel like my emotions were going to get the best of me.

"I think I need to excuse myself for a bit," I said.

Jill obviously could tell I was struggling.

"Go on up and rest," she said. "I've got them and I'll come check on you in awhile."

Even as I was getting emotional I also felt better that Jill was back home. I went upstairs and just collapsed on the bed and fell asleep. I awoke to Jill stroking my cheek and looking at me. I looked up to her and she looked as beautiful as ever to me.

"The kids are watching a movie," she said.

She continued to look at me as I fully awoke.

"I'm sorry," she said. "I don't think you were ready for that and I should've considered that more than Ben's situation."

"It's ok," I said somewhat truthfully. "Were you ready for it?"

Jill didn't respond as she continued to caress me and look in my eyes.

"We promised each other transparency," I continued. "Remember?"

She nodded.

"Umm," she began. "Yeah, I was ready."

"Did you know that before you left?" I asked.

"No," she said. "Not entirely."

I waited knowing she would continue.

"I didn't start to feel it until I was shopping for the dress," she said. "Till then it was really just helping Ben out. But as I shopped and tried things on it started to hit me what I was doing. I was shopping to look as good as possible for another man. And not just any man, a man that I am intimate with whom I really enjoy being intimate with. I was so wet I masturbated in the dressing room between trying on dresses. I came again in the shower before you came up and saw me. And then when I saw you stroking yourself I thought you might be in the same place as me."

She paused before continuing.

"And I saw you the whole time," she said. "I never intended to shave myself bare until I saw you watching me and I decided I needed to see how you would respond. I knew you would connect me going bare to what Ben likes so seeing you cum the second I started to shave my strip convinced me this night was a turn on for you as well."

I just continued to look at her not knowing what to say.

"So was I completely wrong?" she asked.

"What do you mean?" I replied.

"I mean did it turn you on at all or was it a miserable experience?" she asked.

"I don't know," I stuttered. "I mean..."

"Did you cum again?" she asked.

I nodded.

"How many times?" she asked.

"A few," I responded truthfully.

"Before or after Ben sent you the pictures of me and us together?" she continued.

"After," I answered.

"And after the video I sent?" she went on.

I just nodded again.

"I know you feel strange about it," she started again. "But it's ok. The emotions we're going through are all new. They aren't right or wrong, just new."

"I want to be mad," I said truthfully. "But I'm not mad. Last night I felt jealous though for the first time."

"I hope it doesn't sound mean that I am kind of glad you do," she said. "That way I still know I mean a lot to you."

Our conversation paused for a bit.

"I can see you are hard right now," she said. "Aren't you?"

I hadn't even noticed but I certainly was so just nodded.

"Well I'll let you decide if you want to know anything about last night or not," she said. "It's totally up to you."

Ultimately I needed to know and continue to be in the know and have transparency if this was to work and to know when we might be getting into a dangerous area so I felt like Jill should tell me everything.

"I don't want to ask questions," I started. "So just tell me everything from when you left until you got home."

Jill paused for a few and smiled at me lovingly.

"Ok," she started. "The second I took my ring off I felt like a different woman. I could feel myself getting wet in the car. Five minutes down the road Ben texted me his room number. I didn't want to text him back while driving so I just called him. He sounded happy to hear my voice and said he couldn't believe I was going to be his date. Of course that comment made me feel good."

Jill described the rest of the phone conversation.

"I'm excited too Ben," I said. "And I have to tell you something."

"What is it Jill?" he said.

"My totally bare pussy is fucking dripping wet right now and the second I get to the room you need to fuck me," I told him.

"Jill my cock has been so hard all day since I knew you were coming," he said. "Don't worry I am going to fuck you better than I ever have."

Jill continued about the call and arriving at the hotel.

The rest of my drive there we basically talked dirty to each other and I just had to try not to wreck the car. When I finally parked and got to the room the door was cracked and I walked in and Ben was staring at me naked stroking his massive cock, which looked bigger than ever. I peeled off my clothes at the door and he was deep inside me in no time. We fucked hard for about thirty minutes and I had cum twice before Ben exploded inside me."

We both rinsed in the shower just to clean our bodies off and then started to get ready. We got done and had about 45 minutes before we had to be downstairs and were going to go to the bar and have a drink but I needed Ben's cock again so we started kissing and I fished his cock out of his pants and went down on my knees to suck him off.

She continued.

That's when you called. At first I didn't want to answer but when you kept calling I wanted to make sure something wasn't wrong. Once I realized there wasn't anything wrong I knew why you called and that spurred me on to suck Ben even harder so you could watch him cum down my throat. I thought that would do it for you.

"You ok?" she asked me and I nodded.

Then I got freshened back up and we went downstairs. Ben introduced me to his colleagues and everything was great. They really took to me and were impressed and kept complimenting Ben on his taste in women and I of course played Ben up as well. The evening was going very good and I told Ben to send you a couple of the pictures we had taken. I let him pick which ones.

Jill continued.

I got along great with the CEO of Ben's company who was a woman my age. We hit it off and the VP was a female too. As drinks flowed conversation was typical and then the jokes started to turn into those of a sexual nature as more drinks flowed. They were all married but shared freely and Ben tried to be a total gentleman and not kiss and tell until his CEO really put him on the spot.

"Ben I have been around a long time," she began. "And you don't land a woman like Jill here just because you are a wizard with computers. So tell us your secret."

Ben squirmed and tried to fake smile but really didn't want to say anything so I knew I needed to come to his rescue.

"Well," I started. "Ben is a computer wizard for sure. But if truth needs to be told here he is also the best damn fuck I've ever had in my life with a cock that won't quit."

"I knew it!" his CEO exclaimed. "Good for you Ben."

They all toasted him as I rubbed his knee to let him know it was okay. Whatever his reputation was before last night it is now that and then some with upper management. But the conversation got me so damn horny I couldn't stand it and I reached down and felt that Ben's cock was rock hard so I told the table to excuse us for a moment.

I dragged Ben to the nearest place I could find which was a supply closet and we started fucking. He told me he wanted to film it so I told him he could and so we traded off holding the phone as we fucked. It was the most animalistic sex in my life and a completely new feeling and experience. It was also the most explosive orgasm in my life.

We tried to straighten ourselves up as best we could but the second we got back to the table it was obvious.

"How you feel Jill?" his CEO asked.

I just smiled and gave an honest reply.

"I've never cum so hard in my life," I said. "Now I need another drink."

I thought it was a good idea to start texting you and seeing if you were still awake. I regretted that this morning but in the moment it felt like a good idea. The rest of the night was fun. We danced, we laughed and I made sure Ben looked like a hero. When we got back to the room we were back at it and after cumming a few more times I was spent and then Ben unloaded inside me for his last time of the night.

After that I crashed, hard. We both slept from about 3 AM till we woke up after 10 AM this morning. Ben woke up with a raging hard on as expected but I was still too sore and spent so I offered him a hand job which he was happy to accept.

Ben started telling me how amazing I was and how amazing it felt to have me on his arm last night and that it was hands down the best night of his life. He showered me with compliments as I stroked his enormous cock. He looked like he could never be happier in his life. I was caught up in the moment and when I could tell he was close I spoke for the first time.

"Ben," I said.

"Yeah," he responded.

"I love you," I said.

And with that he exploded rope after rope of cum. He came harder than I had ever seen him and was almost panting afterwards as I just smiled at him as I laid his cock across his stomach.

"Jill," he started. "Were you serious about that?"

"Yes," I said. "I do love you Ben. But you have to understand it is a different kind of love than I have with my husband and family. My love for you is with someone that has come into my life that I am so happy and blessed for and I hope that makes sense and hope that you can accept that limit to it."

"I definitely understand," he said. "And it is more than I could hope for given the circumstances. But I definitely love you too. And I love your husband as well.

"Then I better get ready and get back to him," I said. "I know last night could not have been easy on him."

"I'm sure it wasn't," Ben said.

That ended the long detailed recap of the events that had unfolded.

"You need to know what I said to Ben I meant," she said to me. "I do love him. But nowhere near how I love you. It is separate. I love you unconditionally. I love Ben just as someone who has come into our lives. Does that make sense?"

I nodded that it did.

"So I guess it was a good night then," I said.

"Yes it was," replied Jill. "But there could be one problem."

"What's that?" I asked.

"Well Ben's CEO liked me so much that they have invited Ben and I to their beach house this summer and don't want to take NO for an answer," she said.

"What are you going to do?" I asked.

"Well we have time to figure that out," Jill said. "But for now, I think things with all of us need to settle a bit. Let's launch this company we've been working so hard on. Let's continue to have fun and explore as long as we're both comfortable. And who knows what tomorrow will bring."

It sounded like the only reasonable plan to consider.