Chapter 1

I couldn't believe what I was seeing. My brown eyes were glued to the television, my mind lost completely. The disembodied voice of the announcer started again, "Once again, the lucky numbers for tonight's Powerball Lottery are 2, 11, 22, 26, 41, and the powerball 39."

My hand began to tremble as I brought the ticket back into my eyeline, and then I threw up. The rest of the night was a blur of fantasies, dreams, and delusions of grandeur. To celebrate, I threw back a six pack of beer, two bottles of cheap wine, and smoked a blunt or two.

Here I was, 25 years old, and I had just hit the biggest jackpot in the history of the powerball. I laughed at the fact that I probably wouldn't even remember when I woke up the next day, before staggering into bed.

The next morning arrived with that familiar, yet still very shrill beeping coming from my alarm clock. Like most mornings, I knocked it off my bedside table and had to search through a pile of dirty laundry to find it. Finally, I got the horrible automaton in my hands, switching it off before tossing it back into the cloth monster's waiting mouth.

I reached into the back pocket of the ratty jeans I still had on from the night before - terrified that last night was just a dream. My fingers delicately wrapped around the paper in my pocket, and my eyes closed instinctively. After a bit longer than a standard blink, they opened again revealing that last night's events actually took place.

Grabbing my cell phone off the table, I rushed out to my beaten up 2001 Honda Accord, heading to the nearest lottery office to claim my winnings. As I put the car in drive, I pulled out my phone and called off work, making some excuse about a family emergency. My prize was in my sights, and the nagging realization of what would eventually happen crept in.

It was rather ironic that I would receive such an amazing windfall shortly after discovering that I was what is known as a "paypig". For some unknown reason, I had recently become obsessed with giving beautiful women untold amounts of money, just for them to call me names, humiliate me, and ignore me - all while refusing me the right to orgasm. Logically, I know it makes no sense to pay a woman in the Internet $100 to tell you how to jerk off but not cum, but nothing made me as excited as this did.

I had been interested in domination, and femdom in particular for years now, but had only discovered the excellence that is "Findom" a couple of months before hand. I had been watching jerk off instruction videos for a while before I came across one starring my favorite Domme titled "paypig humiliation". I watched the video the first time with confusion and apprehension.

Over the next few weeks, my curiosity got the best of me, and I started jerking off to the video again and again. Each time was like the best high I had ever had from any drug. The orgasms were plentiful, and very voluminous. I was getting hooked.

I tried finding findommes on Craigslist, and omegle, but I didn't have much luck until about three weeks into my exploration. I connected with a woman who identified herself as Princess Krystal, and she had me sitting with my dick in my hand, and my paypal account open in another window within minutes.

I typed in her email address, and the tribute she requested of $50. I was rock hard and leaking as I hit send. She thanked me immediately for not wasting her time, and allowed me to start stroking to a picture she sent me of her in a bikini.

As I stroked, she asked about my kinks and fetishes, and my brain immediately responded with a list of things I would never want anyone to know. The necessary blood that my brain required to think before speaking wasn't available unfortunately, so I told her all about how I had a small penis, and liked to be dressed up and treated like a woman (also known as the sissy fetish). "Stroke faster pig."

As I obeyed, she started to ask me more personal questions, "When was the last time you had sex with a woman? Have you ever sucked cock before? What's the worst secret you have?" My mind rambled off all the answers before I could even question why she wanted to know. Before I could think too hard, another message came up, "I really love Florida, especially the Orlando area."

My heart skipped several beats, almost exploding it felt like. I stopped stroking and had to process what I was reading. "Yeah, Florida is all right if you're just passing through." I tried to play it off calmly.

"Don't lie to me, piggy... " was the message captioning a photo of my Facebook page. I threw up quite a bit when I saw the picture. After making sure there weren't anymore after shocks coming, I retreated back into my bedroom where another message awaited me, " You wouldn't want this sent to your mother would you?" below was a collage of chat messages, pictures I had sent, information about my job, and more.