I was getting on in years. I know 45 is not that old, but when you’re alone it feels much older. I had been successful. Very much so. Starting my own law firm at 33 and running it well for 12 years meant I didn’t have to worry about money anymore. That was nice, but my life felt empty. Felt alone and meaningless. That’s when I met Cassie.
I was shocked at first that a girl like her would be interested in a guy like me. She was twenty years younger than me and quite attractive. Brunette with a lithe body and just enough tits. I wasn’t dumb. I figured she was probably after my money. The truth is I didn’t care. I just wanted to be with someone.
I proposed to her after six months of dating. I told her I didn’t care if she loved me, she could have everything I had if she’d just be with me.
She laughed at me. It hurt like you wouldn’t believe, but only for an instant. She told me she wanted more than my money and my heart perked up.
She said she knew what my problem was. She said she’d seen my dreams. Her eyes started to glow and my skin started to crawl. I ran my hands over my body as it shifted and changed. Tits bloomed on my chest, hair cascaded down past my eyes, my hips widened and tore my pants while my ass ballooned outwards. I looked up at Cassie, a change as I used to tower over her by 5 inches, and she was smiling down at me. She had turned me into a woman.
My heart raced. I’d always wondered what it would be like to be a woman. Fantasized about it. Now here it was, tits, pussy, and all. I looked at Cassie, my face no doubt blank with confusion. I had so many questions, but before I could answer them Cassie began to explain.
The change was not permanent. It did not alter reality, so as a woman I had no identity. She told me she would marry me, and that during the week I would continue to be myself, earning money hand over fist for us. On the weekends she would turn me into this beauty. After a few more years of being married she’d change me permanently and the old me would “die”. She would inherit all my money and we’d move some place tropical.
The only problem, I learned later, was that I wasn’t a lesbian. Breaking this news to Cassie nearly made me sick with worry, and it took me another six months to build up the courage. Six months of turning into a woman on the weekends and having lesbian sex that left me unsatisfied. Six months of sneaking off to masturbate and fantasize about fucking guys. I knew everything was going to fall apart when I opened my mouth. It was a week before our wedding when I told her.
To my surprise, Cassie laughed at me again. She said she wasn’t strictly speaking a lesbian either, but was bi. She said we’d make it work.
We made it to our hotel room on our honeymoon and I felt sick with anxiety. Cassie’s eyes glowed and I turned into a woman again. I opened the suit case Cassie had packed for me with all the women’s clothes I’d bought only to find it empty. She told me I wouldn’t be needing clothes this trip. The door bell rang and Cassie told me to open it.
Now here I am, losing my virginity to the bellboy while my wife watches and masturbates. It feels so strange, but so good. Even while the stranger fills me and thrills me with his cock all I can do is think about Cassie masturbating over my shoulder and feel my heart leap into my throat. I don’t know that I’ll ever prove that I deserved her, but one thing I was sure of was that I loved her.