Sandra talks first

Before I could get a word out, Sandra smiled up at me broke the silence that had formed between us. “You’re a hell of a lover, John,” she said dreamily, moving to kiss my cheek with her luscious, full lips. “But even you have to admit that all of this is a bit of a surprise… not only the fact that you’ve suddenly come into a great deal of money that you’re freely spending on me, but also that you’re about to marry my daughter, that you saw a side of me that no one else has… and that even then you still decided to come tonight.”

“I guess… I guess it just felt like the right thing to do,” I replied. She smiled sweetly at that. “Why don’t you start by telling me how you came into that money, then? You don’t mind, do you?” she asked cautiously, but I smiled back at her. “Of course. I suppose that’s only fair given all that’s happened tonight…”

So I told Sandra about the grand prize I had won off of a lottery ticket, how it was more money than I had ever seen in my entire life, how excited I was to spend it and share it with those close to me. “Except, instead of telling your fiancé about your new fortune… you chose to spend it on me, instead,” Sandra realized, a blush forming on her cheeks. To be fair, I was beginning to blush myself. “I-I just wanted to have some fun before tying the knot…” I explained hesitantly, but Sandra’s deep, warm chuckle melted away any anxiety I felt. “Whatever your reasons, hun,” she said, and I could swear my dick jumped up when she called me ‘hun’, “I am /extremely/ flattered and /extremely/ honored that a handsome, kind, generous man like yourself would choose to spend his time with me,” she whispered, sitting up to press against my chest, my hands wrapping around her wide hips and fat ass as her breasts pushed towards my face. I gazed up at her as she spoke and felt enraptured by her words. She smiled seductively and gave me a wink. “Why don’t we go on with it as planned then, hm? After all, we have this entire penthouse to ourselves, three days to spend between us, and hundreds of thousands of dollars to do whatever we want.”

I grinned up at her and gave her ass a squeeze; she moaned in response. “That’s exactly what I was thinking, babe,” I said, and Sandra grinned even wider at the use of the word babe. It’s a term I hadn’t ever used with Sandra, only ever with Sarah… but right now it felt right to say it. So why not go with what my heart was telling me? It was only for three days, after all.

“Good,” she said, and tilted her neck forward to kiss me. I inhaled her scent and memorized it: roses and champagne. “In that case, tomorrow will be the official first day of our three scheduled days together, which I have elected to call “Girlfriend Day” given the character and activities you requested in your note.” Sandra beamed at me. “I’m so excited! I was thinking about this all the way on the flight over - and the two other days as well, of course,” she said.

Sandra’s excitement was palpable, and I could feel it spreading to me as well. Girlfriend Day - while a bit on the nose, I had chosen for it to be a day of shopping at luxurious stores and enjoying fine dining - the kind of dates that I would always hope to give for Sarah when we were still dating, but I’m now able to provide for her sissy father-in-law instead. It was a crazy turn of fate, but ever since winning that lottery ticket I’ve learned not to question my luck and just go with it.

Sandra and I had a quiet rest of the night, sharing deep kisses and stories of our time with Sarah - comparing our own feelings and experiences with Sandra’s daughter and my bride, and how they had shaped us. Perhaps it was better that the sissy I was having a brief affair with was my fiancé’s estranged father - how else would I have learned all of things about her?

Our talks were not all so serious, though; copious amounts of weed and **** were consumed between us, leading to even more lurid and lewd discussions, which resulted in the two of us drunkenly making out while we each stroked each other’s cocks; that was a new one for me, but it was just as exciting as my sex with Sandra, and feeling her cum coursing through her sissy clit as her tongue explored my mouth and shot out all over my bigger, thicker cock was unlike anything I had experienced before.

Eventually, Sandra and I became sleepy and we both made our way to the king size bed that felt much better than the one I had been sleeping on at home; I would have to see about finding out what brand the hotel furnished this penthouse with. Feeling Sandra’s big, fat, beautiful body pressed against me, her head resting against my chest was everything I needed in that moment. “Mm… goodnight, John,” she murmured sleepily, pressing a kiss to my hairy chest. “Goodnight, Sandra,” I replied and closed my eyes happily as so drifted off to sleep, dreaming of the erotic adventures Sandra and I would be getting into the following day…