The top floor

The elevator ride up to the top floor was undoubtedly the longest elevator ride I had ever been on. I had texted Sandra that I had arrived to which she informed me that she would be waiting for me inside. This was it. After many months of flirting and mutual lust, my deepest fantasy was about to be fulfilled. There was no going back once I entered that door, and I knew this. I was about to cheat on Sarah, my fiancé and the woman that I loved, with her cross dressing escort of a father. Even so, I just knew that I had to do this; this was just a one time thing after all, and once our three days were up, we could go our separate ways and life would go back to normal. At least, that’s what I keep telling myself.

The elevator dinged, and there I was. The top floor. Never before had I elected to spend so much money on accommodations, but this was truly a special set of nights, and with the million that I had now it just made sense to go all out. I found my way to our room and stood there a moment before finally entering. The lights in the expansive front room were set low, and all throughout the suite soft, romantic music played to set the mood. “Sandra?” I called out, waiting to here her voice. “I’m in here!” she called out sweetly, and I followed the sound towards the bedroom, the door just slightly ajar. Pushing it open, the sight that greeted me made my cock swell in an instant.

Sandra was on the bed, laying on her side facing towards me, wearing a red satin neglige that hugged tight along her fat belly and along her thick, milky white thighs. She still wore the light brown wig which looked so natural and sexy on her, along with eye shadow, mascara, blush, and a delicious shade of red lipstick; all made up, she looked like a true lady, which was unlike Sarah, who preferred a more youthful appearance. She smiled at me and invited me in with her gorgeous brown eyes. We said nothing to as I approached the bed, both of us just watching each, admiring each other’s forms and the lust that had formed between us. In an instant we were mere inches from each other as I knelt forward on the bed. My right hand moved to caress her thigh while my left I felt drawn to touch her cheek. We stared back and forth at each other for a long moment, and I could feel my heart beating through my chest. This was it. My left hand traveled down to cup along her thick chin and I drew closer slowly, never looking away from Sandra. Our lips were centimeters apart. “John…” she whispered softly, reaching a hand to gently hold my head. “Sandra…” I whispered, and leaned forward and closed my eyes as our lips pressed together for the first time. Our first kiss. All I could feel in that moment were the fireworks going off in my heart and my cock throbbing in need for this sissy. I pressed forward and our first kiss became our second kiss, then third, fourth, fifth, and many more afterwards. We couldn’t stop ourselves; we were like teenagers, making out like it was the first time. Every time I pushed my lips forward in want, she would push back with equal passion, and soon the room was filled with the sounds of our lips smacking together over slow, sensual music. It had only been a few minutes, but it felt like we had been kissing for hours when we finally broke away from each other, her eyes dancing with delight as I stared back at her, and her smile looked as warm and genuine as mine felt. “Hey, stud,” she said, stroking her hand along my own thigh. “Hey, princess,” I replied, lost in her eyes, relishing the taste of her lips. “That was even better than I could have imagined,” she said huskily, that deep voice resonating along her with her sultry tone. “I completely agree,” I said, and thought about how much better it was compared to my first kiss with Sarah. I was completely mystified by this elegant sissy whore who I was holding in my arms, who I wanted to keep holding in my arms for as long as possibly, feeling her fat body pressed against mine, groping and caressing her ass and thighs.

Sandra had other plans though as she pulled me in by my tie, my lips smashing against hers as I crawled after her, kicking my shoes off to the floor as I went. “I want you, John,” she said in between kisses, “I need you.” Her hand reached down to stroke my shaft through my pants, and my own hands instantly went to take off my belt and pull down my pants and underwear, freeing my eight inch manhood to be grabbed by Sandra’s soft hands. “Oh, fuck,” she quivered as she felt my hard cock, and I followed suit with a moan in her ear as I rushed to take off my tie and shirt. “You’re even bigger than I thought,” she said breathlessly, and I was above her now, our hips close together as her red neglige fell back along her fat belly and revealed her shapely legs, her throbbing cock locked in its cage, wrapped in the very same black lace panties that had gone missing from my fiancé’s underwear drawer a week ago. I pulled away from our passionate kiss after some considerable effort on my part in order to pull aside her panties and line my cock up with her hole. My cockhead touched the rim and her pussy quivered and winked in response. “Yes, John!” Sandra moaned into my ear, her hands feeling all along my back as she spread her legs wide for me. Her hole yearned for my dick to enter it, to penetrate her fully and absolutely, and I was in no state to deny such a need. “Fuck, take my pussy, make it yours!” she moaned, and that was all I needed to hear.

Pushing my cock forward, what little resistance there was at first gave way as Sandra’s hole practically pulled me in. “Fuuuck,” Sandra and I both moaned, each inch of my fat cock sliding deeper inside of her with each passing second. I had never felt anything like it; Sarah absolutely refused to do any kind of anal, so I was only able to imagine what it would feel like, and it never came close to how it felt to be inside of Sandra. It was like heaven for my cock; warm and wet within, it was tighter than any other pussy I had been inside and it kept gripping me in further, deeper until eventually I was balls deep inside of my sissy whore. Sandra and I stayed like that for a few moments, both of us breathing fast as we looked back at each other, moaning in pleasure as she continued to adjust to my cock. “Alright, I’m ready,” she said, looking back up at me with lust in her eyes, “fuck me like a whore, stud.” Not even a minute after going balls deep and Sandra was already ready, which was far faster than it took Sarah to accommodate to my length. Sandra really was something else.

It didn’t take long for me to find my rhythm, and soon enough I was pumping in and out of Sandra’s tight sissy pussy at a rate and passion I had never been inspired to perform at with anyone else. My heavy balls were smacking against her fat taint, and all throughout the room our combined moans were creating a symphony of sensual noises. Again and again I hammered into her hole and watched as her eyes rolled back into her head, and how her little sissy clit leaked cum even in its caged state; truly, Sandra was in much bliss as I was, only further supported by the fact that our tongues were entwined almost the entire time, continuing our make out session from before. This was everything I hoped for and more, and I could have gone on all night if I was asked to.

That being said, after ten minutes of constant fucking in that position, I felt myself picking up speed as my orgasm was coming close. “Fuck, Sandra I’m gonna cum!” I moaned, to which she snapped open her stunning brown eyes to look at mine. “Cum on my face, John,” she said as I continued to rail her pussy. “Claim the whore you spent $25,000 dollars on,” she said, and that was all I could take. Feeling my cum rushing, I pulled out of her hole, leaving it gaping after my thorough fucking, and rushed to move my cockhead to her pretty face. In an instant two shots came out from my dick, landing on her lips and cheeks, to which she smiled eagerly. “Fuck, yes,” she moaned as I shot out more cum, coating her entire face with the pent up load I had been saving for her for a day and a half. When I was finally done, I looked down at my work and marveled at how beautiful Sandra looked covered in my cum. I think she could tell I was impressed as she looked up at me and winked before licking at the cum all over her face. “Thanks, John,” she said, before taking my hand which had some cum on it and started sucking on them to clean them.

When she was done, I fell back, exhausted but extremely satisfied. When she crawled down to lay next to me, I felt even better, her head on my chest, her arm around my waist, her eyes looking up in to mine. I could feel her heart beating fast next to mine - this was an incredibly strong connection we were having. There was something I deeply wanted to say, it was on the tip of my tongue, but I couldn’t figure it out…