Shopping, of course

Sandra was quick with breakfast, in that she had ordered some room service for the both of us. We shared a laugh and ate together before getting dressed. Sandra wore this amazing yellow sundress that flowed along her wide hips and fat ass, complimenting her red wig exceptionally well. Truth be told, Sandra in all her glory still could be easily identified as an aging, fat man in drag and excessive make up, but this only made me want her more. The fact that she was also my soon to be father-in-law only enhanced the experience. With a sensuous, lingering kiss on my cheek, Sandra slipped her heavy arm around mine and pressed her ample curves against me as we left the hotel room and ventured downtown; I was a man flush with excessive cash, after all, so why not spend copious amounts of it on my sissy whore?

We must have been quite the sight when we walked through the lobby, a younger, handsome man walking arm-in-arm with an obese crossdresser in a yellow sundress. I saw a few people look our way, but most people seemed to not mind our presence as a couple. It felt good. Sandra was as confident as ever as we exited the hotel and stepped to the sidewalk where a limo was waiting for us. Okay, maybe this purchase was a bit excessive, but it was totally worth it to see the expression on Sandra’s face when I told her it was our ride, especially the deep blush on her cheeks when I followed in after her.

“I had no idea my boyfriend had such luxurious tastes…” she said, stretching out the word boyfriend as she spoke. She leaned against me as the limo pulled away, and I smirked back at her. “Anything for my girl,” I replied. I could tell she really liked being called “my girl” because she leaned in quick and pressed her lips to mine. Not only a few hundred feet from our bedroom and we were already hungering for each other again. We made out for minutes at a time, groping each other’s bodies as we drove around town. Sandra was in my lap and grinding her body into me by the time our limo stopped, and we pulled away from each other with some regret, breathing fast from our foreplay. “Guess we’ll have to continue this later,” she said with a smile before leading us out from the limo.

Without the need to worry about how much all this was costing me, shopping was swift and joyful. We spent several hours exploring the stores downtown, the both of us trying on different things while the other watched and gave their opinion. I loved watching Sandra try on all sorts of expensive dresses and then buying each of them for her, knowing that she would be wearing them for me. The part I loved even more was our stop at a lingerie shop, where Sandra told me I should buy her multiple sets of the lingerie she wanted in case I ever wanted “tear them right off of me.” I quickly agreed and shared my newfound wealth with that lingerie shop several times over.

At one point while Sandra was trying on some clothes, I stopped by at a jeweler nearby. My heart was thumping in my chest as I approached the counter with the intent to buy a diamond engagement ring so that I could “propose” to Sandra tonight; it was part of my fantasy after all and both Sandra and I had agreed to it, though I didn’t tell her about when I was planning to pop the question, so to speak. Still, I was supposed to be getting married to her daughter. What was I doing here? The guilt almost seemed to overwhelm me into leaving before a store manager finally noticed me standing there and approached, eager to sell me something.

“And how can I help you sir?” he asked.

“Uh, I would like to buy a ring. An engagement ring, actually.”

“Wonderful! She must be a very lucky lady,” he said, taking me over to a nearby counter. I chuckled to myself but followed after him as he showed me the rings; I saw one that looked similar to the one I proposed to my fiance with. It was a nice diamond, sure, but wouldn’t it make things more complicated for my emotions if Sandra was wearing a ring so similar to Sarah’s? Quickly, I looked around for an alternative. My eyes spotted it, and the shine that this ring gave almost seemed excessive; it seemed about twice the size as the one I gave my fiance and was more than three times the price I paid for the other. Not wanting to waste any more time and risk Sandra catching me in here, I chose the gleaming diamond ring that was twice the size of my fiancé’s and paid for it in cash; I had to say, it felt extremely liberating to be loaded and spending my money on the finest whore I could find; maybe others disagreed, but I knew what I wanted.

Leaving the jewelry store with my secret in hand, I caught up with Sandra just as she was finishing up at the checkout. She gave me a loving kiss on the lips as we met and took my hand in hers as we walked through downtown. We ended up watching a matinee at the local movie theater, where Sandra gave me an expert handjob in the cover of darkness as she leaned against me, my arm wrapped around her shoulders like two lovers. I had to cover my mouth as I erupted into her hand, my eyes rolling back into my head as she whispered into my ear how much she wanted me to cum for her right then and there. She giggled softly as she leaned down and cleaned my cock with her mouth before licking each of her fingers in delight.

When we got out of the theater, she looked to me with a smile. “So, what next?”