The following is a work of fiction. It is not based on any real events or people. It features a 20-something crossdresser and an older man, with more men to "come" in later chapters. I hope you like it and welcome your feedback at amysissy96@hotmail.com. Enjoy!
Category: Transgender / TV
Saturday Night is Date Night, Part 1
by Amy
Getting my own place changed everything. I went from sneaking a quick dress-up whenever my housemates were out to being able to dress whenever I wanted, and in whatever I wanted. During the week I had a new routine. I'd get home from work, shower and slip into a new sheer babydoll and lacey thong, and enjoy the shivering pleasure of rolling sexy stockings up my smooth legs. I'd spend the whole evening dressed like this, flirting with guys on my favourite hookup sites. I'd play with myself, stroking my smooth cock and teasing my tight little hole with my vibrator. I'd watch my favourite porn too and pretend I was the girl being gangbanged by strange men or the schoolgirl seducing her older teacher. The weekends were different though. Saturday was date night. But I never left my apartment. Every Saturday night a different guy would show up at my door and I'd invite him in for our date. Sometimes they'd stay the whole night, but other times they'd leave when they were done and I'd have enough time to arrange a second date. This particular Saturday, I didn't know a lot about my imminent date, other than that he was in his 50s, was 6-foot tall, and had a bit of a belly visible in the only photo he'd sent me--a photo of his thick, hairy and very erect cock. Oh, and I knew he was going to be my father.
Not my real father, of course! On my online profile, I ask my prospective dates to pick a fantasy scenario that we then role-play when they arrive. I started doing this because I think it makes the whole interaction less awkward. But really because I find it really, really hot. The scenarios are pretty cliched, but that's kinda the point. The guys know what to expect from them and they establish up front that I'm going to be submissive to them. There's a schoolgirl/teacher scenario where I'm being punished for misbehaving. There's a blonde bimbo scenario where I play dumb and will do anything he says. In one, I'm a virgin bride all in white and he carries me to bed on our wedding night. In another, my date becomes a neighbour who catches me crossdressing and tries to blackmail me. Maybe my favourite scenario is the one we're enacting tonight.
The door buzzes and I let him in to the building. I leave the front door ajar and disappear into my bedroom to wait. I'm wearing a black miniskirt that leaves nothing to the imagination, a loose hot pink tank top with the word "Princess" printed on the front in glittery silver, black fishnet stockings, heels and a studded leather jacket. It's very bubblegum punk, perfect for the bratty, rebellious teen daughter I'm role-playing. I hear him enter the apartment and grab a beer from the fridge. That's my cue.
"I'm going out," I announce, walking out of the bedroom and towards the front door without even looking at him.
"Hey!" he shouts. "I just got home, don't you have a kiss for your father?"
I roll my eyes and turn around. He's not bad looking, but not what I'd describe as hot, either. A worn, weathered face with a slightly grizzled close-cropped beard. Salt and pepper hair. Thick arms, broad shoulders, solid around the waist. He looks like he used to play sport or have a physically demanding job, but doesn't do either as much any more. I can tell I'm several inches shorter than him, even in these heels. I walk over to him and give him a reluctant peck on the cheek.
"Satisfied?" I pout.
"Not until you tell me where you're going."
"I said. Out."
"Out with who? Because you're not going out near any guys dressed like that."
"I don't have to listen to this," I mutter and turn to leave again. But he grabs my wrist and pulls me close. I can smell the beer.
"You're gonna listen because you're my daughter. And no daughter of mine is gonna leave this house dressed like a slut."
His grip on my wrist is strong. It's starting to hurt. I can see real anger in his eyes. He's getting into this.
"You can't stop me," I say, trying to sound defiant, but obviously failing.
"I'm already stopping you."
I try to struggle free but he's much too strong. He lifts his right hand and slaps me hard across the face, knocking all the breath out of me. Still gripping my wrist, he pins my right arm behind my back then clamps his right hand around my neck, lifting my now reddened face to look at him. I force a couple of tears to well in my eyes, urging them out to help my mascara run down my cheeks.
"And now we're gonna find out what happens to slutty little girls who try to defy their daddy," he says, just inches from my face.
He drags me to the couch. I stumble in my heels and it's only thanks to the strength of his grip around my neck that I don't fall over. He sits down and pulls me across his lap, face down, ass up. His left hand now pins my head to the couch while his right slips under my miniskirt to expose the pink g-string wedged between my plump round cheeks. At first his rough hand feels almost gentle as he squeezes my ass, but then he raises it and spanks me hard. Shockingly hard, in fact. My gasp is genuine. He strikes me again and again and again, hitting harder with each blow until I'm squirming and whimpering and just starting to wonder if this might be getting out of control. But then I realise my little cock (my little clit?) is rock hard pressed against his thigh and I'm sure he can feel it too.
That's the end of chapter one. I'll have chapter two for you soon.