Forgive me if the tags are wrong. This is a fictional story about a father-in-law and a closet crossdresser. If that offends you, please carry on…
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I slipped off into the garage while everyone else filed in through the front door. My feet ached. My pride was tired of bouncing between senses of freedom and embarrassment.
A few groups of older, too grown to still be trick-or-treating folks passed by along the sidewalk, each oblivious to me sitting alone in the dark.
I found a joint my father-in-law stashed beside the ash tray, lit it up and admired myself as I crossed my legs. It had been a long night.
The deadbolt on the door into the house turned suspiciously behind me. The door creaked open. I glanced over my shoulder in time to recognize my father-in-law’s silhouette as he crept out into the garage.
I crossed my legs the other way, the slit in my dress falling open to reveal my thighs. The nylon on my legs finished whispering as his footsteps approached. The smoke began working its magic.
My father-in-law had two glasses in hand. He stopped beside me and held one out.
“Here,” he said unusually soft. “Trade?”
I felt my cheeks flush as I looked up towards his face, my eyes briefly skinny-dipping within his. He smiled and carefully took the joint from my fingertips as I took the glass from his.
Our fingers touched. An uncontrollable urge clenched my thighs together.
“This here ain’t no beginner’s luck,” he said through a smile, his voice still soft and affectionate. “No fuckin’ way you ain’t dressed up befo’.”
He took a step back into the shadows to take a long, audible hit from the joint.
I sipped the glass he had handed me. Whiskey. A smile stretched across my now tingly face. My thighs squeezed together again. My pantyhose started feeling silkier and more sensuous as the smoke intensified.
“What makes you say that?” I asked, my voice an octave or two too high. “Your son made a bet, loser dresses like a woman for Halloween, and here I am, the loser.”
“We both know you did this befo’,” he answered quickly, leaning toward me to pass the joint back. Our fingers touched again. Time hiccupped. Something shifted inside of me. All the awkwardness and embarrassment from earlier in the night faded away.
“No way you lost some random bet and six months later you dress up and look like this,” he continued. “How much money you put into that?”
“I dunno,” I thought for a moment. “Four or five hundred.”
“Five bills on a bet?!” He choked on his drink.
“Takes a lot of work for me to look like this,” I practically whispered as I put the joint back to my red lips. I took a drag. “How long did it take for me to come out the bathroom? Like two hours?!”
“Time well spent,” he said satisfactorily, adjusting himself as he spoke.
I pretended not to notice. I took another hit before offering it back. My father-in-law refused.
“Get higher,” he laughed.
I shifted my body toward him in the chair and re-crossed my legs as seductively as I could. The slit in my dress fell open again. My eyes bathed deeply inside of his gaze while his eyes navigated the topography of my thighs. I recognized a gleam from his appreciation.
The bud popped as I took another, and I exhaled a cloud of smoke into his direction.
“I’m higher,” I smiled.
My father-in-law gathered our empty glasses and went inside the house without a word.
(…to be continued)
Source: reddit.com/r/sexystories/comments/ga0e65/halloween_bet_part_01_mtdrugs
Part 02
My father-in-law found me standing beside his motorcycle, using the little bit of streetlight that filtered through the canopy of trees outside to touch-up my makeup. I should have been cleaning up, changing and heading home to be with my family, but I felt compelled to freshen up for his return.
“Do Elvira take pics?” he asked as he stepped out into the garage with four glasses of whiskey in tow; pairs of glasses pinched together with his fingers on both hands. He made his way over to me, his words slurring rhythmically as he spoke. He’d unbuttoned his work shirt and he didn’t wear any kind of t-shirt underneath. “Er’body gone or ‘sleep,” he said happily.
I dropped the lipstick back into my clutch, took a glass from his hand and sat down in my chair, slowly crossing my legs for our mutual pleasure. His attention, my big hair, heavy makeup, huge, fake breasts, tight dress, girdle, the drinks, the smoke and especially the silky layers of nylon on my thighs were all coming together to bring a new level of sensuality to life. One that pumped relentlessly throughout my system.
“And your wife?” I thought out loud, reflecting on his question. I failed to scrutinize the choice of words until they became audible. She was my mother-in-law, after all.
“Coma-fuckin-tose,” he said triumphantly with a pearly grin plastered across his face. “Beer and meds and she’s in my shit all night. Liquor and prescriptions and her ol’ cranky ass out cold ‘till the sun come up!”
I sipped my glass while he leaned back against the cabinets and rolled another joint.
“It’s cool if not, but Elvira looked wicked standing by my bike,” he said before sealing the paper with his tongue. “Jus’ sayin’.”
I sipped some more, stalling the conversation while my mind took two separate trips into the future. Down one road, my father-in-law had pictures of me dressed up and the world slowly but surely turned against me. On the other, we looked back on a weird night where the two of us had fun and bonded.
He leaned over to pass me the fresh joint. I needed it. I’d shared pictures with strangers before, but I’d never dressed up in front of anyone. I’d snuck down the driveway to grab the morning paper and I’d sat out on the back patio in the middle of night, but I’d never entertained the idea of getting to dress for someone, for another person to take pictures of me in person.
“With your phone?” I finally asked as I exhaled a cloud of smoke between us.
“Stand up,” my father-in-law said in the soft, affectionate voice he used earlier in the night. He stepped towards me, still an inch or two taller than me despite the stilettos. It was an awkward time to realize how much larger he was. His proximity and my frailness together made it seem like he could absorb me without much effort.
“It’s okay,” he whispered again, cupping the back of my neck with his hand.
I cocked my head to the side, my eyes burying themselves in the chiseled skin beneath his shirt. His fingers caressed my hairline a bit. I instinctively placed an open palm on his chest. The contrast of my pale skin and fiery red fingernails popped against his skin tone. I climbed his neck and face with my gaze until our eyes connected. His mouth hovered near mine.
“It’s okay,” he repeated, his lips so close to mine I could feel the words roll off them.
“I’m sorry,” I said softly, my lips blindly feeling back for his.
As we stood there, his palm resting on the back of my neck, my hand planted against his chest, I anticipated the sensation of his lips pressing softly against mine. I imagined the traces of red lipstick left on his lips as our mouths wildly felt for each other’s in the dark.
I wanted him to kiss me.
I needed him to kiss me.
But we had a photoshoot to negotiate.