A Paypig's Journey
Chapter 1

Copyright© 2015 by Worthless PayPiggy

BDSM Sex Story: Chapter 1 - Part fantasy, part reality. The narrator gets himself into hot water with a Financial Dominatrix. Codes are for entire story.

Caution: This BDSM Sex Story contains strong sexual content, including Ma/Fa   Ma/Ma   NonConsensual   Blackmail   Slavery   BiSexual   CrossDressing   Fiction   BDSM   DomSub   FemaleDom   Humiliation   Sadistic   Oral Sex   Masturbation   Sex Toys   Water Sports   Exhibitionism   Size   Foot Fetish   Slow  

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.

"No, please. Don't do that Princess, please." I literally got on cam and begged her not to expose me, while on my knees wearing panties, stockings, and full makeup.

"What's your reputation worth, slut?" I hesitated, which was stupid considering she was watching now.

"Anything Princess. I'll do anything!" I begged and pleaded with her. After minutes of silence on her end, she finally asked me how much money I had in the bank right now, and demanded a screenshot for evidence. I sent it to her, and she laughed at my pathetic $200 balance.

"If you'd like to buy your freedom and dignity, I suggest you send every last penny to my paypal in the next 10 minutes. Understood?" I nodded in defeat, before sending the last of my hard earned money to her. She called me a good boy and sent me another picture, this time of her ass in the bikini and told me I could cum to the picture. I thanked her and disconnected, hoping to never hear from her again.

When I finally started stroking again however, I wanted nothing more than her instruction. I jerked my pathetic cock hard and fast until I finally shot the biggest load of my life all over the place. I cleaned up, cried, and then crawled into bed. That is how my obsession began.

I stepped back and stick to reading stories, and watching videos about findom and blackmail fetish stuff. It was enough to satiate me until I hit the lottery.

Within a couple of weeks, I had received a lump sum of $475,000,000 give or take. I tried to be responsible, putting some of the money into a savings account. Of course, I lavished a bit - a new house, new car, quit my job, and the usual stuff that people blow their money on. I had spent just under a million of the massive award before the itch returned.

I went on cam sites and did the whole phone sex thing, but it wasn't real enough. I just felt as though I wasted a couple thousand dollars. My orgasms had been dull and lifeless for weeks by that point, and I knew exactly what I was craving.

Trying to be smart, I jerked myself off about 15 times, hoping to bury the urge in post orgasm shame, but even that didn't work. After feeling like I hadn't truly cum in over a month, I couldn't take it anymore. My hands shook as I pulled out my new debit card and entered the details into paypal.

I knew I needed to submit to Princess Krystal. I just had to find a way to get her attention, since she was no longer responding on kik or email. Sweat droplets landed on my keyboard as I typed in her email address, and a note asking her to reconsider my worthiness as a pay pig. I moved the cursor to the payment amount slowly, trying to remember to breathe. "Are you sure you wanna play with fire again?" I thought to myself, but my little dick had taken over. My fingers deftly worked the keyboard until the field showed $1,000.

Immediately, my hand found my dick as soon as I hit send. I was stroking furiously, thinking at least I'll have something to think about while I jerk off for a while, when a response email showed up in my inbox.

"Pathetic little Piggy,

It looks like you're finally ready to get serious about submitting to a Goddess aren't you? You got my attention ... Now let's see if you can hold it ;)

Princess Krystal"

I was so close to cumming that it hurt to stop, but I knew that my cock already belonged to my Princess. I wouldn't dare waste her time again. I switched back over to paypal and readied another $1,000 payment. I included another note:

"Princess Krystal,

Thank you so much for allowing me some of your precious time. I swear I won't lose your attention again, no matter what. I'm ready to be owned completely. I am your property Princess.


I sat back and waited, counting the seconds until I would hear from my goddess again. I stroked my pathetic cock as I waited, being careful not to cum. After what felt like hours, she sent another mail.


You've at least piqued my interest for the night. Add me on Skype at 'username', and do it quick, the night is coming to a close."

My fingers have never moved faster than when I logged into Skype and added Princess as a contact. Moments later, she appeared online.

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