Sissy fiction i guess i love ladyboys

crossdress

So a few hours later I was in a very interesting position. Hopefully the only interesting position I
would be in that night. Not only had I transformed into a woman a few months earlier, not only
was I now going on a date with a man, not only was I very excited about going on a date with a
man, but I was going on a date with my worst enemy. The thought of it was so ugly and repellent,
and yet I couldn’t wipe the fucking smile off my face. What was I doing to myself? Was it some-
thing to do with my new body? There was this strange excitement running through me that I
couldn’t control. He’d been there, and then we were talking, and then he left with my phone
number.

The old me fought well and hard, he didn’t want me to go, he begged me to stay in my chair, or
lie on my bed and play video games. But he’d been a bitter guy, angry and hate filled. I couldn’t
feel anything but excitement. I couldn’t feel anything but the promise that I was going to have a
good time. I dressed as well as I could, surfacing a dress that had been bought for me mostly as a
joke, finding some heels and prepping my makeup as carefully as possible. This was the first time
you could say I’d ever dressed like a girl.

crossdress

My parents were over the moon when they found out I had a date, though they had naturally as-
sumed it was with a girl, as that had been my preference once. I didn’t know if that was still the
case in that moment. When I mentioned it was a man they were a little taken aback, but gave me
their support anyway. I had been kind of hoping for a little push back, a part of me had been
anyway, so I’d have a reason to blow him off. Now it was looking like I had no choice but to blow
him.

Jokes. But still, thoughts like that were very prevalent in my head. Thoughts like that gripped me
with fear and adrenaline and sweet arousal. I was doing something I’d never done before, with no
knowledge of how it was going to turn out. I’d been turned into a woman, but I’d never acted like
one before, never dressed like one, never loved like one. I was hoping for things to go slow no
matter what happened. I hadn’t made my mind up about what I thought about such a strange situa-
tion.

He picked me up in his Porsche, which I had not been expecting. He was wearing the fanciest suit
I’d ever seen, and kissed me lightly on the cheek when he received me. I felt so exposed in that
dress, but he made me feel calm. I got in the passenger seat, and saw a girl in the mirror. She
looked so beautiful and content Butterflies. Butterflies everywhere.

We rolled up at the most expensive restaurant in town, and were escorted to our own private
dining room. I knew he was rich, but I never knew how much. As it turned out, he’d been very suc-
cessful in professional boxing, something i’d never been interested in before. He’d stopped me in
the street because he’d never seen someone quite so lovely as me. I blushed, but he pressed on.
Serious. He had never seen someone who so piqued his interest before. He asked me what I wanted
in life, and for a second I stumbled, not knowing what to say.