Video call with Sandra

Things were looking on top of the world for me. For the first time ever, I could look into my own bank account and see not just six but seven figures looking back at me, all but ensuring complete financial security once I went public with it. Then Sarah and I would be free to pursue whatever it was we wished in comfort and style - all after I get a chance to enjoy myself, of course.

Sandra’s response to my $25,000 tip was immediate and incredibly provocative: only a few minutes after the money cleared through, I received a video chat request from Sandra. By then I was already back home and in my and Sarah’s bedroom while she was still out, so I wasted no time in accepting her chat request, my heart beating fast and my dick hard inside my pants.

In a voice noticeably a bit deeper than most women yet with lightness that was undoubtedly feminine, I heard her. “Hey there, stud,” she said as the video finished loading, which revealed Sandra in her bedroom, all made up, in a blonde wig and wearing nothing save for my fiance’s black lace panties, her little cocklette straining inside her chastity cage. I could feel myself grin as I looked upon my sissy whore in all her beauty. “Hey there, princess,” I responded, and I could tell that her sissy clit throbbed at my words. Sandra moaned and rubbed her hand along her massive thigh. "You've never failed to surprise me before, but I have to say this is a new high for you, John," she said, and the way she said my name was drawn out and sensual - I often heard it most from her when she was moaning it in audio messages she sent to me, so unconsciously I reached for my own cock and started jerking it through my pants. "I had a look at those extra services you purchased... you're a very naughty man, and all for ol' me?" she intoned sweetly. "And three of the ILY specials, too... just that alone will pay for this month's rent! You've always been my favorite donator but this is really something else," she said.

I felt myself swell with pride and a more than a bit of shame; here I was, about to cheat on the woman I loved and was going to make my wife with a sissy whore who I just spent $25,000 on. I tried not to let it show, but I think Sandra could tell I was having mixed feelings. Giggling, she shimmed herself along her bed to reveal something she had been hiding from me. "Remember this? I finally decided to take it out of storage, just for us," she said; it was the very same wedding dress that I had first seen her in, the introduced me to the account SissyBBWSandra and then later the sissy whore I came to know as Sandra. My heart started to beat as fast as I was jerking my dick, which I had since pulled out and was stroking openly for Sandra to admire. "How could I forget?" I replied, looking back to her from the wedding dress as I admired her fat and curves. I could tell that she could feel my eyes on her, because she turned around got on her bed on all fours and presenting her massive ass to me, once again with my fiance's panties stretched out widely along her hips and almost completely hidden in her crack. "I know waiting two days to finally meet will be tough for the both of us, so how about we get one last session in now before I have to leave for my flight?" she asked, already beginning to shake her ass back and forth for me. I moaned in response as I gripped my cock tighter and stroked myself even faster. She spanked herself and moaned out my name, sending ripples along her jiggling ass that only further aroused me. "Fuck, say my name, stud..." she moaned out as she continued to shake and spank her perfect, round ass. Over and over I said her name aloud, moaning along with her as I reached closer and closer to my climax.

Just then, I heard the sound of a car door slamming shut and its doors being locked, and so did Sandra through the call. My fiance. "Shit," I groaned, and took my hand off my cock. Sandra laughed playfully and turned around to look at me. "Don't worry, stud; keep that load saved up for me and I will milk it out of you just like you deserve. And in a proper wedding dress, too!" I could only smile at the thought of finally getting to partake in my deepest, most passionate fantasy in as soon as two days. "I'm looking forward to it. I'll keep this load just for you, princess," I said, which earned me a deep, adorable smile from Sandra; I could tell she was excited about all of this too. "Bye, now," she said sweetly, blowing me a kiss as I moved in to close the call. God, how I couldn't wait to finally get to kiss those lips.

"Bye," I said, almost regretfully, and turned off the call.