Sarah's past and Sadie's future. (Alternate history for Sarah)

When we got back to Sarah’s place… to home… Sarah walked in with her usual confident pace. I followed, my steps small and unsteady in the raised heels she insisted I practice in. "Keep those on," she called from the kitchen, her voice firm yet caring, "You still need the practice, and they're the most comfortable you'll have."

My feet ached with every step, the unfamiliar arch and pressure reminding me of the day's discomforts. But I obliged, meeting her at the kitchen table where she awaited with an intensity in her eyes. Before I could speak, she raised a hand, signaling for me to listen. "I need to tell you my story, no interruptions. Just listen," she urged, her voice softer now, **** for the first time since meeting her.

Sarah's tale began with her own confusion growing up in a traditionalist family, her journey through the Internet's vast corridors, her realization that she wasn't interested in women, but drawn to androgyny and femininity in all its forms, but mostly to those that were males on paper but looked like anything but.

"Before I knew who I was," Sarah started, her eyes distant as if visualizing her past, "I tried to fit into what everyone else seemed to want me to be. My first girlfriend... it was what you'd expect, the guy dating the girl next door. But inside, I felt like I was acting, playing a role that never quite fit. It was confusing, to say the least. I felt more connection to the erotic feminine men online than to what I was actually living."

She paused, a sigh escaping her lips as if releasing the weight of those days. "College was where things started to change. I met people who were different, who didn't fit into neat boxes, closer to the type of relationships I was reading and fantasizing about. I had a few flings, each one pushing me a bit further, making me question what I really wanted, who I really was."

"The real turning point was meeting someone androgynous, they could pass as women or man. They would treat me like their girl when they were dress like a man, I'm sure it was a joke at first." she continued, a small smile playing on her lips. "And They were beautiful in a way I couldn't explain when dressed like a women, not confined to any gender norms but able excel in each. It was eye-opening. For the first time, I felt a connection that went beyond the physical—it was emotional, aesthetic... it resonated with something deep inside me."

Sarah's gaze turned inward, reflective. "Then, I dated a trans woman. She was like a mirror, showing me parts of myself I had tried to ignore. We shared experiences, fears, and dreams. It was deeply transformative. I started to see my own future in her stories."

"As I began to embrace myself, to start my transition, my relationships changed too. I dated a sissy. It was liberating, affirming. I could be myself, explore my dominance, my femininity, all of it at the same time, not piecemeal anymore. It felt right, like I'd found a missing piece of myself."

She leaned forward, her eyes locking onto mine. "Right when it felt like I found the right fit, it feel apart, we had a safe word but they never used it. Then one night they left while I was out, when I came back there was just a note, apparently every time I made them top me, it tore a piece of them away, it felt like when they were with their exes and had to pretend to a top and in charge dominate male. That the only reason they stuck it out as long as they did was because I was acting like a power bottom when it was happening."

As she spoke, her fingers occasionally drifted down to her waist line before stopping and coming back to where they had been, before doing so again but not stopping this time, and pulling her hem down showing to me to my shock, a tiny and cute chastity cage, holding a leaking cock. "This," she explained, gesturing subtly, "helps me keep focused, especially during streams. It's on a timer, only comes off when it's scheduled. It's part of how I stay balanced in the 'right' mind set to rake in the big bucks. Now I'm worried it's made me ruin things again."-

"I don't actually like men but when I'm horny enough I can pretend. I may seem like a wanton bimbo airhead sometimes but I only really want to be with femmes that used to be men. Its why I kissed you, everything we've been doing has been turning me on something fierce, and for a second my brain thought we were 'together' together like all my other 'boy'-friends. But your not, you're only doing this because its the best way I can help you make money, I know you've been getting turned on as well but I also see the confliction and confusion in them too."

As Sarah shared her story, the careful balance she maintained between her public persona and her private desires. My mind was a whirl, but she wasn't done.

Sarah looked at me with a new intensity. "I see parts of my own journey in you," she confessed, "And I won't lie, it's exciting. But I want to be clear. This isn't just about me or my desires. It's about helping you like I promised, and for forgetting that I am sorry."

She stood, her movement fluid and deliberate, and walked around the table to where I sat, frozen in thought. "I'm not here to **** anything on you," she continued, her voice firm but gentle. "But the way I see it, you have three choices, and I won't hold it against you which ever you pick." She counted off with her fingers as she laid everything out.

"First- Leave now, I won't hold what I spent already against you and won't take the con ticket from you, but will offer to buy it at an inflated rate to help you off set the loss you're still going to have to deal with." Not an option.

"Second- I continue to treat you like a protege I'm mentoring and try to keep my feelings in check, we move forward like that kiss never happened." I was liking the sound of that as even if she paid a ludicrous amount for the ticket I would still be up shit creek, just with a paddle.

I started to zone out as she paused to breath, I was almost in a spiral of dark thoughts thinking of how screwed I would be without her, before zoning back in when I saw a slight blush creep up her cheeks as she finished.

"Or three- I still help you like I was going to but as my girlfriend. To be clear, my submissive girlfriend, I maybe a switch but you have along way to go before I would even let you play at being a top."

Her words hung in the air between us, a mix of offer and challenge. I took a deep breath, considering the weight of it and my decision.