A Night With Daddy
by Pamela
It happened the night I went to a costume party in a warehouse in a run-down neighborhood. I didn’t know anyone there, but I’d been trying to break out of my shell, craving a human connection. Partygoers were practically falling over each other in a crazy maze of garish rooms, black lights and cramped hallways. The DJ was nuts. The girls volunteering behind the bar were more drunk than the patrons. The whole thing was a playful riotous confusion of sights, sounds, colors, textures, and bodies. I went up to the rooftop bar to get some air. The patio’s string lights complimented the view of the sparkling lights of the city.
I was dressed in drag as the artist Frida Kahlo. It was an uncanny resemblance. Frida and I have the same ethnic background - Mexican and German. Heightening the realism was the fact that I’d recently started trying out female hormone pills and testosterone blockers. They were the kind that transsexuals took - for people who wanted to permanently change their physical gender. I was still working out why I’d been drawn to explore this. I thought of myself as a boy who loved to dress up as a girl sometimes. Because I just liked it. But I was still a boy and nothing would really change that. I told myself the pills were an experiment. Would they make dressing up as a girl easier? Would I like the way they made me look? They way they made me feel? They had already softened my skin and smoothed out my facial features. But I was scared of going too far. People would eventually notice. My job. My parents.
Up on the roof, I ran into a man I knew. He was dressed as Zorro. He was the ex-boyfriend of a friend of my ex-girlfriend. You know how it goes. How many degrees of separation in a city like this? He had a reputation in my friend circle - a dominant 'daddy', straight as an arrow, very possessive, into the S&M scene. He was much older than me and had a thing for younger women - women my age. He worked out and had a great body. Salt and pepper hair. He always wore black, usually in leather pants. He was there alone that night, which was unusual. It turned out neither of us knew anyone else at the party.He struck up a long conversation with me. I had been trying to talk in character as Frida all night, but I dropped it with him. I’d been using it as a mask with strangers, hiding my social anxiety. All my life I’d tended to shy away from straight men, including him, fearing ridicule, disgust and rejection. The scars of middle and high school. I had a feminine demeanor and it always managed to shine through, despite my attempts to suppress it. But tonight, with him, I didn’t try to hide anything, and it felt comfortable, one on one. Man to woman. After a while I suddenly realized his arm was around my waist. I was surprised and confused, but played it cool, wondering if it even meant anything. I realized I was desperate to feel what his girlfriends had felt, to know it, to embody it, to make it real, make myself real through this connection. He smoothly guided me back behind the tall bamboo walls separating the party area from the rest of the empty rooftop.
The next thing I knew, I was down on all fours, skirt pushed up, panties yanked forcefully down, getting fingered from behind. First one finger.. then in slid a second one... just as he was going for a third, a voice cut in: "Is that real!?" A very drunken reveler had wandered astray, and was standing over us. He was obviously confused to see Zorro fingering Frida Kahlo, who had a cock. "Yes it’s real. Now go away." I hissed. The drunk stumbled off, dazed.Zorro whisked me off in his convertible, over the bridge, to his boxy modern loft. It seems he was actually attracted to me, the girlyboy. The idea was so far fetched I couldn’t believe it was happening. And yet it was. He played frantic sex games with me all night on the couch. It was as if he believed he had just one shot at performing acts he’d never do again. The mutual release of pent up desire.
He held Frida’s hand. My hand.
"So tell me, why do you like pretending to be a girl?"
"Well...” I countered. “Hormonally... I AM a girl now."
Reflexively he pulled his hand away, as if he suddenly realized he was holding a snake or fire. "Why are you taking female hormones?"
I struggled to explain my feelings. "I'm experimenting. I want to see how it feels. Find out if it's right for me." For the first time, the words felt weak, wrong somehow.
We rode the rest of the way back in silence.
I was confused by him. Did he like me better when he thought I was a boy dressed as a girl for kicks or kink, rather than a girl in a boy's body? He didn't understand me, I thought. But in that moment, I suddenly understood myself.
He dropped me off at home, and I never heard from him again. But I knew in my heart he was the first man I was ever with as a woman.
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