Money Troubles - Chapter 1

The Proposition

I was standing in the kitchen trying to figure out how to save money. Since I lost my job last week, I’ve been trying to come up with a plan. I went to the grocery store and bought the cheapest meals I could find. Ramen noodles, boxed rice, and a few cans of soup. Stacey walked in and looked over my shoulder.

“What the hell is this?” she asked in disgust.

“What does it look like? Food.” I replied.

“What, food for prisoners. You’re kidding me right?” she asked. Stacey and I have been married for 4 years. She has always been the take charge one in the relationship. She has been working as an event planner for the last 8 years and loves her job. I was a computer programmer but was recently laid off because my company decided to utilize AI to write their programs. It was a shock but I didn’t think it would be a big deal because I had worked at the company for 10 years and had plenty of experience. Well, turns out that the industry is changing quickly and nobody is hiring.

“What’s your problem? This is what we can afford right now,” I responded.

“Well, I would have preferred a heads up before I came home to you making us eat like homeless people. This is disgusting. Why don’t you listen to my advice. You need to get a new career,” she said.

“You think I haven’t been trying? Its not that easy.” I shot back.

She rolled her eyes. “I told you to get out of the computer industry 2 years ago. I saw this coming. You think you are smarter than everyone else but here you are with no job, no money, and no clue what to do. I can’t keep paying for all these bills on my own.”

I knew she was right. I was the one that convinced her to buy this big house. I told her that my job was stable and we could afford it. She was the one who wanted to keep the small house and save money. Now she is stuck with a mortgage she didn’t want and I am just sitting around feeling sorry for myself. The worst part is that I have no real skills. I spent all my time programming and didn’t do anything else. So here I am, almost 30 and trying to figure out what to do with my life. Stacey walked out of the kitchen and went to the bedroom. I followed her in and she was taking off her work clothes. Stacey had on a tight blue skirt that showed off her long legs and nice ass. She had on a white button up shirt that was a little see through. Her bra was visible underneath. She had on a matching set of white lace bra and panties. I always thought she had a great body and loved to see her in sexy lingerie.

“Where are you going?” I asked.

“I have to go pick up some stuff at the mall for my event this weekend. You want to come with me? It will give you something to do,” she said.

“Sure, why not,” I replied. I figured it would be better than sitting at home all day feeling sorry for myself. I got dressed and we headed out to the mall. Stacey was driving and I was in the passenger seat. She had on a pair of black leggings and a tight black top. Her blonde hair was pulled back in a pony tail and she had on a pair of black heels. Her legs looked amazing and I couldn’t help but stare.

“What are you looking at?” she asked with a smirk.

“Nothing, just admiring my beautiful wife,” I said.

“Well, don’t get any ideas. I’m not in the mood tonight,” she said.

“Come on, it’s been a week. I’m dying over here,” I replied.

She laughed. “You’ll be fine. You can wait a little longer.”

We pulled into the mall and I followed Stacey inside. She led me to a lingerie store and I immediately got nervous. I have always been shy and never felt comfortable in these types of stores. Stacey, on the other hand, loved to shop here and would always drag me in with her.

“Come on, don’t be such a baby. It’s just underwear,” she said.

“Yeah, but it’s women’s underwear. I don’t belong in here,” I replied.

She grabbed my hand and pulled me in. “Just stay with me and you’ll be fine. I need to pick up some stuff for the servers at the event. The host requested some specific items.”

We walked around the store and Stacey was looking at all the different lingerie sets. She would pick up a pair of panties and hold them up to me.

“What do you think of these? Do you think they would look good on me?” she asked.

I was so embarrassed. There were other people in the store and I didn’t want to be seen looking at women’s underwear.

“I don’t know, whatever you like is fine,” I said.

She rolled her eyes. “You’re no fun. How about this teddy? Do you think this would be sexy?”

She held up a black lace teddy that was see through and had a thong back. I could feel my face getting red and I just nodded my head.

“You’re so cute when you’re embarrassed,” she said with a smile.

She continued to look around and I was just trying to stay out of the way. I was looking at a rack of stockings when I heard a voice behind me.

“I think that teddy would look amazing on you,” the voice said.

I turned around and saw a well dressed older man standing there. He was probably in his 50s, tall, with grey hair. He was wearing a nice suit and had a watch on that looked expensive. I assumed he was talking to Stacey and was about to respond when he spoke again.

“I wasn’t talking to her, I was talking to you,” he said, pointing at me.

I was shocked and didn’t know what to say. Stacey overheard and started laughing.

“He’s right, you know. You would look pretty sexy in that,” she said.

I was mortified. I couldn’t believe she was saying that in front of this stranger. I just stood there with my mouth open, not sure what to do. The man smiled and walked away. Stacey continued to laugh.

“That was hilarious. Did you see his face when he said that? I think he was serious,” she said.

“I doubt it. He was probably just messing with me,” I replied.

“I don’t know, he seemed pretty serious to me. You should have seen the way he was looking at you,” she said.

I just shook my head and tried to change the subject. We finished up our shopping and headed to the checkout. As we were walking out of the store, a big muscular man in a black suit stopped us.

“Excuse me, my boss would like to speak with you,” he said, pointing at me.

“Your boss? Who is your boss?” I asked.

“Tom. He’s the man that was in the store earlier. He would like to make you an offer,” he replied.

I looked at Stacey and she just shrugged her shoulders. I didn’t know what to do so I agreed to talk to him. The man led us to a back room where Tom was waiting. He was sitting in a chair with a glass of whiskey in his hand.

“Please, have a seat,” he said, gesturing to the chairs in front of him.

We sat down and I was trying to figure out what was going on. Why did this man want to talk to me?

“I have a proposition for you,” he started. “I am a very wealthy man and I am used to getting what I want. I saw you in the store and I was immediately attracted to you. I would like to take you out on a date.”

I was shocked. I didn’t know what to say. I’m not gay and I’m not interested in men. I looked at Stacey and she just smiled.

“I’m flattered, but I’m not interested,” I said.

He smiled. “I understand. That’s why I’m willing to pay you. I will give you $5,000 to go on a date with me. All you have to do is wear what I tell you to wear and spend the evening with me.”

I couldn’t believe what I was hearing. This man was offering me money to go on a date with him. I looked at Stacey again and she was nodding her head.

“I think you should do it,” she said. “We could use the money and it’s not like you have to do anything you don’t want to do.”

I was still hesitant. I didn’t want to go on a date with a man, especially one that was obviously interested in me sexually.

“No way,” I said immediately, shaking my head. “Absolutely not.”

Stacey’s hand found my arm, her fingers digging in slightly. “Trey, wait. Think about it. Five thousand dollars. That’s three months of our mortgage right there.”

“That’s not the point,” I sputtered, my voice barely a whisper. “He... he wants me to go on a date with him.”

“Listen to me,” she said, her tone shifting from gentle to commanding. “You’ve been out of work for weeks. We’re burning through savings. This could be a lifeline. Besides, in my world, networking is everything. Who knows? Maybe Tom has connections that could help you find a real job.”

The bodyguard cleared his throat, a sound like gravel shifting. “Mr. Tom is a patient man, but not infinitely so. You have twenty-four hours to decide.” He extended a plain white card to me, with only a single phone number printed in elegant black script. Without another word, he turned and strode away, leaving us standing there like statues.

The car ride home was suffocatingly silent. I could feel Stacey’s eyes on me, assessing, calculating. As soon as we walked through our front door, she broke the tension.

“Okay, let’s talk about this rationally,” she began, leaning against our kitchen counter.

“Rationally? Stacey, he wants me to dress up in... in lingerie and go out with him,” I said, my voice cracking. “How is that rational?”

“Because you’ve been asking me to dress up for you for years,” she countered, her voice dangerously soft. “Do you have any idea how uncomfortable it is to wear heels for hours with pantyhose? How constricting some of those dresses you love so much are? How much time I spend getting ready just so you can have something nice to look at?”

I stared at her, taken aback by the venom in her tone. “That’s... that’s different.”

“Is it?” she stepped closer, her 5’9” frame suddenly seeming even more imposing. “Maybe it’s time you experienced what it feels like to be expected to look a certain way just to please someone else.”

The guilt was immediate and overwhelming. She was right. I had never really considered her discomfort, never thought beyond how her appearance affected me.

“But what if he... what if he wants more?” I asked, my voice barely audible now. “What if he tries to... you know...fuck me.”

Stacey’s expression softened slightly, but only for a moment. Then she leaned in, her voice dropping to a conspiratorial whisper that somehow felt more threatening than her shouting had.

“You remember our trip to Cancun? That night on the balcony?” she asked. “I had on that floral dress and you wouldn’t stop talking about trying something while we were trying to have a good time in town?”

My stomach dropped. I remembered perfectly. We’d been drinking, and I’d been persistent. She’d been reluctant, but I’d convinced her.

“You wanted something that night,” she continued, her eyes locking with mine. “Something I wasn’t comfortable with. But you kept pushing until I gave in. You knew that I had always been scared to try anal with you. But you kept saying that if I loved you then I would let you put it in my ass. Maybe it’s time for you to see what it feels like to be in that position.”

I felt sick. She was right. I had been selfish.

Seeing my reaction, she relented slightly. “Look, I doubt it’ll come to that. Tom seemed... respectable. Wealthy men like him usually have boundaries. This is probably just some fantasy he wants to play out. Worst case scenario is that you end up on your knees in front of him,” Stacey says with a slight laugh.

I stood there, trapped between my pride and my desperation. Between my fear and my guilt. Stacey walked to the counter, picked up the card the bodyguard had given me, and held it out to me. Her eyes met mine, challenging, daring me to take it.

My hand trembled as I reached for the card. I turned away from her, needing this moment to be mine alone. With fingers that felt alien and clumsy, I dialed the number. After two rings, a voice answered.

“Mr. Tom’s office.”

I swallowed hard, my throat dry as sandpaper. “Ok,” I said, the words catching in my throat. “I agree.”