Falling for my Sissy Father in Law

All of this began with a single lottery ticket. I had never been particularly lucky when it came to gambling and lotteries, but all of that changed when I scratched off the grand prize on a $20 ticket I had bought on a whim; in an instant, I had become a millionaire, and for a time I could hardly believe my luck. When I finally stopped shouting and celebrating in my car, I took stock of the situation and realized that I would have to keep this on the down low so as to not ruin things with this newfound and perhaps undeserved wealth; after all, while millions of dollars can open up a lot of opportunities, it could also bring with it many problems.

Chief among them, though, was that if my bride to be ever found out about those winnings, I would probably lose more than half of it in an instant; Sarah had a bit of a problem with keeping her expenses low, often having to dip into our shared bank account to pay for whatever luxury or fad she was into that week. I love her dearly, but in that way she is a bit immature, so I decided then and there that I would hold off on telling her for a while - enjoy a portion of the winnings for myself as I felt I deserved a chance to let loose before our upcoming wedding.

As I pondered what I would spend the money on, I looked down to see an email notification on my phone. It was sent to my private account I keep hidden from Sarah, which I use for some of my more lustful needs. You see, Sarah and I were what you could consider to be a pretty average couple, and this is especially true when it comes to sex. Sarah is a beautiful woman, but she's rather thin and small, and while many men would consider that to be perfect for their needs, it unfortunately wasn't for me - it didn't help that she wasn't interested in exploring love making beyond missionary. For a long time, I didn't know what it was I truly craved and yearned for in sex, until I found her: SissyBBWSandra. That was the name of the sole account I was subscribed to on OnlyFans - and the only person that I could imagine fucking in order to cum while having sex with Sarah.

SissyBBWSandra - or just Sandra, from now on - was truly a big, beautiful woman in the truest sense of the phrase - fat in all the right places, especially her huge, round ass that I constantly fantasize having sit on my face. Many people wouldn't believe that a good looking guy like me with a fiance as pretty as Sarah would be interested in a fat, aging sissy, yet it was those exact qualities that drew me to her in the first place. Her makeup did a lot to help hide her age and wrinkles, but I think those all worked together to make her even sexier. The fact that she had a penis, which was honestly more of a clit than anything else as she always wore a cage on it in the photos and videos she posted, honestly only excited me even more. Every night when I first discovered her page, I would leave Sarah sleeping in bed so that I could jerk off to Sandra's newest posts, often leaving a generous tip on the pieces I enjoyed the most. That was about the time Sandra started to really notice me. We started talking a lot more in direct messages, sexting each other for days on end, exchanging nudes with each other frequently, and often Sandra would send me personal videos and jerk off instructions - which would cause me to blow even bigger loads and send her ever increasing tips. She had quite the following with plenty of other donators and subscribers as I understood it, yet she seemed to take a great interest in me for some reason.

Perhaps it was the fact that the most prominent of the fantasies I shared with her - that I constantly envisioned her in - was of me cheating on my fiance and marrying my fat, sissy mistress. The first picture I had ever seen of Sandra was her in a wedding dress, and in that moment she looked like a proper lady, and the smile that beamed from her face instantly drew me in. Had I the funds and the free time available, I would have gladly paid for her escort fee, along with the many other additions and charges that come along extra that I was interested in. My fantasy seemed to really excite her in the same ways it did for me, which just further fed into our mutual feedback loop of lust that had developed between us.

That's what the email was about; another message from Sandra, which I quickly opened in a heartbeat upon seeing it. There I saw her message: "Hey Stud! Just wanted to let you know I'm wearing your fiance's panties that you sent me..." it started, followed by a photo of her thick, flabby ass taking up most of the shot, showing off her cellulite and stretch marks, and the stretched thin black lace panties that I had stolen from Sarah's underwear drawer; it was the hottest thing I had ever seen in my life, and my dick instantly got hard. This day was turning out incredible for me so far. Below the picture, her message continued: "As it turns out, I'm actually going to be flying out to your city tomorrow (for a wedding as well!) and staying at a hotel. I could be staying at a nicer hotel with a generous tip from you... and maybe we could finally meet and a have a little fun like we always said we would. Think you could get away from your fiance for a day, maybe more? There's so much I want us to do together..."

Fuck. This seemed like it would be my one and only chance to fulfill my greatest sexual needs all at once, but there was still I had a lot to do with Sarah before our wedding next week. I started to think that my luck had turned against me when I received another notification on my phone: it was a text from Sarah this time, informing me that this coming weekend she had to go on an impromptu business trip or risk losing her job. We would still be having dinner with her parents tomorrow night (whom I had come to understand over the years were separated), so I would at least have a chance to meet them together before she had to head out.

Pausing, I sent back a quick reply and sat there in thought once more. Here I was, with a sudden huge influx of money, three days completely free, and a fat sissy I was completely ready to spend thousands of dollars on to have the best weekend of my entire life. Swapping back over to my direct message with Sandra, I grinned as I started to type back my reply: "For you? The best hotel money can buy. Let's make our meeting one to remember," I sent back before returning to her profile to send her his payment for her services; after all, this was merely a professional affair, and all that occurred between us would be kept secret for as long as I wanted it to. Sandra was a sissy whore, but that was just how I liked her. After adding up all the expenses I wanted to and was finally able to pay for, I had a definitive list of my full payment to Sandra which ultimately numbered in the tens of thousands of dollars. On any other day I would have feinted at such a price, but now I had the funds to fully pursue my lustful needs, and Sandra was worth every single penny spent.

With a smile, I sent my $25,000 donation to her with the list of my requests that I was paying for as well as the accommodations we'd be taking at the best hotel in the city. I couldn't wait to finally meet her.

All I had to do now was get through dinner with Sarah's parents tomorrow night and hopefully put on a good face for her father; this was our first meeting together and I needed to make sure everything went according to plan.