What Have I Done? Pt. 01-02

"Yep, big double dog dares, bets, hubby said he bet you would, and so forth. I do remember all that."

So I did another big sigh. "Here's the rest of the story. I am actually torn between doing this dare and just blowing it off as silliness. I have even looked at various ways I could do it and be safe and hopefully have a good experience from it. The big hang-up is the proof."

He just nodded his head and said nothing. He just had a slight smile and a sparkle in his eyes. About then both of our pies and drinks arrive. I spent a few minutes looking at my pie and taking a bite of it.

"Further, I am not sure I really want to do it, but deep inside part of me gets, well, well I react to the thought of doing it. I am so conflicted. I also have a big nagging conflict on why my hubby was almost cavalier about this whole dare thing. I mean when I grew up, getting a double dog dare meant you did it or it would be held over you for like ever." This all came tumbling out of my mouth like my brain had no control at all.

His smile and stare were attractive and kind of sensual, but unnerving at the same time. Finally, he spoke.

"So are you going to tell me more or is this it? You just unburden yourself and gave no more context to it. I understand about the dare, I understand the conflict. You covered that well. You left hanging your thoughts on how to do it if you did it."

"I am embarrassed about that aspect, but here it goes. First I thought of a bar. You know just go to a bar that ladies that do this stuff for a living go to and see if I can do it that way. While a decent option, it seemed a little unsafe. Then I thought of those websites you can advertise yourself at. Again a little better. More control can do some research on the person and all, but still not safe enough for me to be comfortable with it. Then the perverse me thought of just some college boy at one of the bars near the university. He would probably be excited to get a MILF and get it filmed. That seemed a really good option. But they never have money so would have to do role-playing and give him the money to give me on video. Then I said screw it, I do not like any of these. Then the least safe option struck me. I have a dispatch friend for the Sheriffs. I could get a list of the local pimps and see if I could arrange a short night working for them and get some of that filmed. But there are all sorts of unsafe crap with that." With that my non-stop babbling ended.

"So you are going to do this are you not or just what? And only two of those seem reasonable and none seem like you." There was a very long pause as we both ate and sipped on our drinks. I realized he was not much at talking or he was very good at letting me get over whatever I was struggling with.

"Here is how I see it. Your first issue is you have to make a definitive decision on if you doing this dare or not. Until you do that, this is just becoming a frustrating exercise that's making you distracted and kinda crazy." Then he chuckled. He was right though. I had not made a decision.

He went on that there was another option I had not thought of that was safe and met the requirements.

"By the way, I am rich out the wazoo and could easily pay you as I intimated. If that is all you are after, I think there is something more primal you are wrestling with and you are afraid to give voice to. A hardcore businesswoman that keeps everything in check, plans, organizes and runs a business that helps others be as tightly done as you and your business. Your deeper thoughts disturb you because they go against everything you hold as proper and safe and tidy. You like tidy in everything from thought to deed. With this statement done, he went back to eating smiling and making me squirm even more.

All I could get out was a whispered when did you get so smart, I thought you were a trainer. He laughed and said he chose to be a trainer. Then I got the shock of my life. He was like both my parents died in an accident on a trip when he was a sophomore in College. They had huge insurance policies that paid off everything and left him with about three million dollars. While he was depressed and trying to come to grips with that loss he was gambling in small amounts, playing the lotteries, and buying himself an expensive car and a practical car. Then five years ago, a couple of years after graduation one of the lottery tickets hit for a nice amount. Not one of the huge ones but it like 68 million. After taxes and everything for a lump sum, he had about 46 million left and he has spent the last five years investing and protecting his income and money. So again I say if it was all about the money to prove something, I can volunteer.

I was stunned to silence, I am sure my look expressed this also. The only thing I could do was put the last bite of pie in my mouth to prevent my mouth from saying a word. He chuckled.

I finally was able to get out of my mouth, how old are you? He started laughing a full honest amused laugh. He said he was 29, from a mixed-race parentage, and held two bachelor's degrees. I followed this up by changing the topic. I was shocked in my head. My brain just flashed a message that I was becoming attracted to him and I am just a MILF conquest at best.

"Ummm, this one way you said I missed, care to share?"

"Adult amateur video, you know amateur porn."

I was stunned and silent. Not only for the suggestion being good, but it offend all of my moral senses I was raised with. I was getting deeper into moral conflict. I was now getting turned on as one of my secret pleasures was porn. Yes, cheating wife, girl-girl, and big cock. Now I am being suggested to do one-off porn. But the issue is who is going to record it and who will be the guy. Okay, this is getting out of hand.

"Ummm okay, and let's say that's the option I chose how does that work? Do I walk into the neighbor porn makers' business and say hey I want to do just a one-off movie to win a dare."

"No silly, I will set up several cameras around my bedroom and then we come up with some type of a scripted and then we enjoy ourselves for however long you want and then we sit together a couple of days later and cut it into amateur porn."

"Did you just propose we do amateur porn together to win my dare? You know it is for money, the dare. You know that, right?"

"Yes, I do and I will pay you the going rate of 10,000 for a 45 minuter to 90-minute video. I will pay in it a cashier's check like they do in the business and on a business account from one of the businesses I have or make one up."

"Now I am curious, how do you know all this?"

"I have an old friend from high school that's in the business, we still chat. He has told me about the business side a few times."

I sit there for what had to be ten minutes without saying a word, staring down at my empty plate. My thoughts were finally interrupted by the waitress refilling my coffee.

"Okay, I am in, let's make a porn. I now have only ten days to produce the proof."

"The cashier's check will do that, but we might need a short non-graphic clip"