Side Business Ch. 01

My wife, Jill, and I were doing really well. We were in our mid-40's and had a young daughter and had finally reached a point where finances were not a burden and we were starting to enjoy life a little bit more. In fact, Jill had been able to stop working and be at home more with our daughter and when she was at school she was able to focus on some of her hobbies and interests.

Jill has always been a looker but with the additional time for herself she had become somewhat of a fitness nut and her body was showing the results. Always a petite woman she now had some defined muscle and some curves that really popped. Her butt had lifted some and her legs were as tone as I'd ever seen them. With that came some more personal confidence and my eyes were blessed by her wearing skimpier attire around the house -- sports bras, yoga pants, short shorts, sundresses, etc. Jill is 5-1 and 110 pounds, 34c, blonde and blue -- everything a red-blooded man could hope for.

Jill had become more physical and sexual during this transition as well which was an added bonus. I'd say our sex life was good, not great, we aren't all-nighters or going to be mistaken for a couple in porn but we enjoyed each other. It has never been easy for her to have an orgasm but even that was getting a bit easier which only made her desire for sex grow. I think with so much of the stress of working and finances removed from her daily equation she was just a much more relaxed and happy person.

The other hobby Jill had was making jewelry and every time she made something she would get comments on the pieces every time she went somewhere. Everyone always asked where they could buy it and she would explain she made it and it wasn't in a store. This had always been the case but now that she was making more jewelry she got more comments and it triggered an idea that maybe she had a small business opportunity she should look into.

Over the next couple of months we did some research together and decided she should go for it. We had saved up what we thought was enough money to achieve the business plan and she was very excited. My wife would focus on making the jewelry and I'd help with some of the financial aspects of running her business on the side. The one thing we most needed help on was the technology piece as were clueless there.

We knew we'd need a website, help with digital, social and mobile advertising as well as someone who could assist in getting us set up with the ordering system, shipping methods, payments, search optimization, etc. That was a lot of work and we knew without it we'd never get this off the ground and never be successful. We went to a few companies that specialize in those areas and they were so expensive we were a bit deflated as we had hoped to not have to take out a loan. We were also hoping to find a company that could show us and educate us along the way so we could take those roles over as we got a good grasp of them -- that wasn't too appealing to many of those we talked to.

I mentioned our dilemma to a friend who was somewhat techie and he said we ought to see about hiring someone freelance that could work in their spare time. We hadn't thought about that but it made some sense. It would take longer to get up and running probably but Jill could work on the jewelry inventory during that time. My friend mentioned someone at his office, Ben, that might be good for the job -- kind of a whiz with computers -- so he said he'd float it by him and let me know.

A couple days later he let me know that Ben would at least hear us out on what we were looking to do and we could go from there. So I called Ben and he agreed to come by the house and hear our proposal and what we needed. As it turned out he lived only 5 minutes away from us so it was very convenient. We agreed on the next night at 9PM so our daughter would be in bed and we wouldn't be interrupted.

Ben arrived at 9PM on the dot and I invited him in and showed him to the basement which we had somewhat turned into the home office. All of Jill's supplies for making jewelry were there, we had a computer set up that was solely for the business and had everything we thought we needed in that space.

Ben was a very unassuming guy. He was kind of tall and lean, perhaps too skinny. I'd guess early 30's or so. We had just started talking when Jill came to the basement and I introduced them. Jill was just in some workout attire, nothing overly revealing but yoga pants also don't leave too much to the imagination. I could sense Ben thought she was attractive.

We told Ben a bit about us and then asked him to do the same. He was pretty quiet, didn't reveal too much, liked to run and swim, liked to watch college football, liked computers but wasn't overly social. He had no wife, no girlfriend or much going on in that department.

After the small talk we explained to him our business Idea with Jill doing most of the talking about the idea itself and showing him some of the things she had made. I then filled in on the business side and where I thought we needed the most help. Ben listened attentively to everything we had to say and once we were done we asked him what he thought.

Ben started in on what he thought we needed and it didn't take long to know he had been listening and processing and had some really good ideas and insights on how to make the business come to life in the digital world. We were excited about his ideas and agreed with them. A great website to showcase the products as well as process everything was key and step one and reaching the right target consumer via digital/social and mobile was step two. One simple idea he had was instead of just photos of the jewelry itself, show photos with the jewelry on a neck, wrist, model, etc. Simple idea but a better visualization for customers indeed.

Now came the hard part, how long would it take, how much would it cost, could he do everything we needed and most importantly did he want to. Ben told us he was certainly capable of doing what was needed to get to launch but wasn't sure how much time he wanted to devote to it. Since he worked full-time it was tough to figure it out but he liked the concept and said it was somewhat interesting to him to be able to work on something from the ground up. He eventually said he'd be open to helping two nights a week for a few hours.

That was great so now it was down to how much it was going to cost. Ben hummed and hawed a little bit and then suggested $100/hour and figured he'd probably need 100 hours to get done what needed to be done. That was $10K overall and a lot cheaper than what we were quoted so after some quick discussion we agreed. We agreed Ben would come over every Monday and Thursday night at 9PM for a couple hours and do everything on our computer and periodically show us things we would need to know moving forward.

As it was a Wednesday night Ben said he'd see us tomorrow night and we showed him out. What a relief! Jill and I were both excited. The downside was that it was going to take awhile to get it done, but it would be cheaper and hopefully we'd be able to take over and save more money down the line.

Things were going great over the next 4-6 weeks. The arrangement was perfect. We had our family time and would put our daughter to bed and then Ben would come over twice a week and work. We were making great progress and Ben was super-collaborative. We also go to know him a lot better in that time and he was opening up more to us. Jill had started to make sure she had dinner for him those nights which he was very appreciative of. We paid Ben every two weeks for the work he was doing as well so he never felt cheated.

We liked Ben a lot. He was a bit goofy in a geeky kind of way but also funnier than originally thought. Jill was starting to dig into his social life and told him she was going to find him a girlfriend. He would always blush at that and said he never really had one. This was a longer topic one night and it was obvious Ben was just a bit socially awkward around women and lacked confidence. If he could get as comfortable around others as he was us he'd be fine.

At one point Jill blurted out that he's a man and obviously has needs so he has to get them met somehow. Ben blushed hard and she knew she had him.

"Well are you going to tell me?" she asked.

After some lengthy pause and sheepish grins Ben finally spoke up.

"I like going to strip clubs," he said.

Jill and I certainly weren't expecting that response and her mouth shot open in some disbelief.

"How often do you go?" I asked.

"I go at least once a week, usually Friday or Saturday night, or both," replied Ben.

"That's your outlet?" quizzed Jill. "Why not just go meet some girls somewhere?"

Ben did his typical hum and haw again and then came clean.

"I just really like strip clubs. I like all those girls in one place and getting to choose who to spend time with. I love seeing women in lingerie and then seeing them strip out of it for me is very exciting. Plus there is no pressure, it's all transactional. I don't have to worry about anything. No phone calls, no texts, no nothing."

He certainly had a point as far as I was concerned but Jill wasn't as convinced.

"You need a girlfriend and a relationship," she stated. "We're having some friends over Saturday night to grill out and watch football and you're coming over. I'm going to try to find a couple single women to be here."

"That's a great idea," I said. "You love college football and we can hang out without work hanging over everything."

Ben agreed to come over though he didn't look overly thrilled. He was probably planning on going to a strip club that night so we likely busted up his original plans.

Saturday came and we had a handful of people over but Jill was only able to wrangle up one single woman. We tried to introduce Ben to everyone and get him to engage socially but I could tell it just wasn't his thing and I felt bad for putting him in an awkward position. The single woman who Jill tried to get over to him didn't seem interested so that was a busted play. I sat with him and watched the game and we shot the shit. I found out he was a big Florida State fan and told him Jill and I were big North Carolina fans so we talked about that as well.

At 10PM Ben said he was tired and was going to go home. Jill apologized to him that she hadn't been able to get more women there and that the one there wasn't ideal but he said it was no big deal. She gave him a big hug, the first I remember her ever hugging him and it took him by surprise as well. Even accepting the hug looked a bit awkward for him and he blushed a bit. I knew from day one that he really liked Jill, and who wouldn't, so her touching him physically like that was probably a nice treat.

That Monday night Ben arrived and got to work. Jill was a bit late joining us as she had met a friend for dinner. When she got there we both did a double-take at her. She had on tight black leather pants and a silk blouse and heels and looked dynamite. She gave me a kiss and hug and walked over to Ben and put a hand on his shoulder as he went back to the computer and she asked him how it was going.

Ben showed her some updates to the website that were awesome and Jill was very excited. She excused herself to go get more comfortable and returned in her normal workout/lounge attire. Small talk ensued and drifted to college football.

"You know Florida State and North Carolina play this weekend," I said.

"Yeah that's right," replied Ben. "And we're going to kick your butt."

"Not this year," I responded confidently. "You should come over and watch it with us. We'll grill something up and enjoy the game -- just the three of us. It's the least we can do for all the hard work."

"And I promise I won't try to force any awkward introductions," laughed Jill. "Besides otherwise you'll end up at a strip club wasting your money."

I laughed at that saying, "She's got you there."

"It's not wasted," said Ben with a grin. "But okay I'll come, just don't be upset when my Noles win big."

"Great -- it's settled," I said. "Game time is 7PM so come over at 6 and we'll eat and have a good time."

"Until the game starts," Ben chuckled.

We finished up for the night and got back after it on Thursday. We reaffirmed plans for Saturday night. Our daughter was staying at Grandma's house so we told Ben to just come over when he wanted.

Ben showed up a bit early on Saturday but that was fine. He had a Florida State t-shirt on and said he was ready to rub it in after the win. It was great that Ben was getting so comfortable around us and showing his personality.

Jill walked down the stairs not knowing Ben was there yet and just had a towel wrapped around her with her hair still wet. She freaked when she saw Ben and his jaw about dropped.

"Shit," she said. "Why didn't you tell me Ben was here?"

"Well I didn't realize you were coming down in a towel," I said.

Jill scurried back up the stairs a bit embarrassed.

I looked over at Ben who was still watching that direction and thought I saw him adjust himself ever so slightly.

"She has nothing to be embarrassed about," I said. "She was covered."

"I didn't mind," laughed Ben and I joined in.

We started eating and drinking and game time was approaching. As it did so did the smack talk from all three of us -- all playful in nature. Jill is normally not the smack type talk so the fact that she was getting into it was kind of funny to me and proof the alcohol was kicking in.

"I bet this game isn't even going to be close," bragged Ben.

"Oh yeah," Jill replied. "Care to put your money where your mouth is buster?"

She was getting carried away now and I just let her go.

"You want to make a bet?" asked Ben.

"Sure," said Jill. "Unless you're scared."

"I'm not scared," said Ben. "What do you want to bet?"

You could tell Jill was thinking it over and I literally had no idea if she even knew what a normal bet was. I was prepared for her to say $1 after all that and I would laugh. When she finally spoke I was surprised at how bold she was.

"How about a week of free work?" she said.

Now it was Ben's turn to be surprised and he was obviously taken aback.

"You scared?" taunted Jill.

"No, but I was expecting something along the lines of a case of beer or bottle of booze," replied Ben. "That's like a $400-$500 bet."

He was right about that and figured Jill needed to lower the stakes.

"So you are scared, aren't you?" Jill retorted.

"I just don't have anything to request as my bet that is worth that much," replied Ben.

"Well I think I proved my point," Jill said happily.

"Not so fast," responded Ben. "Give me a second."

There was something about the silence that followed that should've given me greater pause. Jill had backed Ben into a corner and he was trying to think of a way to save face. Finally Ben broke the silence.

"I want a strip tease and lap dance," he said.

Now it was Jill's turn to be shocked.

"What?" she responded. "You want me to pay for you to get lap dances?"

"No," said Ben. "I want a strip tease and lap dance from you."

I wasn't totally positive that is where Ben was going when he first said it either but now it was clear. What wasn't clear was if he was trying to get Jill to back down from her bet.

"You want me to give you a strip dance?" she asked incredulously. "I can't do that."

"Well you said to think of something and so that is what I'd want for a free week of work," Ben replied.

I had become an innocent bystander at this point not sure how to interject when Jill looked at me for help.

"Don't look at me," I said. "You started this."

Jill looked back at Ben and said, "Ben, I don't even know how to do a strip dance so you probably wouldn't even like it."

Without hesitation he responded, "Trust me. I'd love it."

There was another long pause between everyone before Ben piped up again.

"Look, we don't need to bet. But if I'm going to make a bet where I could risk losing more than $400 I would certainly want something like that in return. I wasn't trying to make you uncomfortable, you guys are great and I think you are beautiful Jill so it just popped in my head. And since you guys already know I love strip clubs I figured I'd suggest it."

There was another delay.

"What would I have to do?" asked Jill.

"Well normally that much money would last me a couple nights at a strip club but I'd settle for 30 minutes," replied Ben.

"Yeah but what would I have to do?" Jill asked again.

"Dance for me," replied Ben. "Put something nice on and then you'd slowly dance in front of me and then take your clothes off."

"I have to get naked?" she asked.

"No," said Ben. "But most dances end up topless. I'd let you keep on your bra if you wanted."

I couldn't tell if Jill was seriously considering this and was personally unsure how I felt about it. On one hand it was no big deal she was just going to dance in front of someone and basically strip down to what amounts to a bikini. On the other hand she is my wife.

"Where would we do this?" asked Jill.

"We can do it on a couch or chair, they would work best," Ben replied. "You can turn the lights down some, put on some music."

"How close do I have to get to you?" asked Jill.

"That is kind of up to you," replied Ben. "In the club the girl can touch you but you can't really touch the girl. They get very close and will rub themselves on me during the lap dance part. I know to behave myself."

"What does that mean," asked Jill.

"It just means that I know not to do anything I'm not supposed to do and not touch," said Ben.

I looked down at my watch and realized the game was about to start.

"Look you two," I said. "It's time to make up your mind because the game starts in five minutes and I want to focus on that.

Jill grabbed my hand and led me to the other room.

"What should I do?" she asked.

"I don't know," I replied. "You wanted to bet and you asked for a lot."

"But if Carolina loses and I have to dance for him is that going to be weird and are you going to be mad?" she asked.

"No I won't be mad," I said. "It will probably be more awkward and funny for all of us than anything. Besides I've never seen you dance like that either."

I could see Jill's mind was racing and her heart was pounding and she knew it was probably better to call off the bet and just deal with Ben giving her grief over it. She then walked back into the den and stared right at Ben. He looked up at her with an almost challenging expression. He certainly had the upper hand.

Jill held firm and broke the tension. "Thirty minutes, lights dimmed, I'm not getting naked, you don't get to touch in exchange for two nights of free work."

Ben just nodded and Jill replied "Okay."

Holy shit I thought to myself. She went through with it. It was kind of a no-brainer for Ben. It was just his time if he lost. Yes it was lost money but Jill was literally going to have to "expose" herself to an uncomfortable situation in the case of a loss.

"Oh my GOD," Jill belted out. "I can't believe I just made that bet."

We all laughed.

"I'm going to need more to drink just in case," said Jill. "Who else needs one?"

All hands went up and by the time Jill got back the game was underway.

There was amazing tension and jibes going back and forth throughout the game. Every time Carolina did something great Jill referenced Ben's indentured servitude that loomed and every time Florida State did something great Ben pondered Jill's wardrobe selection for his dance. The good news was that all was in fun and we were all laughing and every jibe and jab.

The game itself was great and competitive. One team would take the lead and then the other. It was tied at halftime and the tension only mounted as we got late into the 4th quarter with Florida State ahead by 7. Jill was very nervous and paced a lot while Ben sat in the couch watching the game intently. Oddly enough not a comment on the bet had been made in the 4th quarter as the stakes were becoming real.