Saturday Night is Date Night Ch. 01

Story Info
Amy has a date with Daddy.
2.6k words
4.53
18.2k
21

Part 1 of the 2 part series

Updated 06/10/2023
Created 09/16/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
AmySissy96
AmySissy96
103 Followers

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 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.

"What happens to slutty little girls who disobey their daddy?" he growls, just inches from my face.

They get hard, I think to myself, all-too-aware of how turned on I am. And they get fucked by Daddy's big dick, I hope. But I'm role-playing here. I gotta remember to stay in character.

"They promise to be good?" I whimper, keen to demonstrate that I've already submitted to him.

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.

"They do," he says, "But first they have to be punished."

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 it moves across 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. My little cock is rock hard pressed against his thigh. I'm sure he can feel it too.

As suddenly as it started, the spanking stops. Daddy's hand is gentle once more, squeezing my stinging and no doubt bright red cheeks with tenderness. He lifts my head so he can look me in the eyes.

"Now what do you say?"

"I'm... I'm... sorry... Daddy," I tremble, all doe-eyed. The tears I've manufactured for this moment are almost genuine. I can tell he's enjoying the authenticity of my performance. "I promise to be a good girl."

"You promise?"

"Yes, Daddy, I promise."

Delicately, he brushed the hair from my face and pulled me up into his arms. I found myself sitting on the couch, snuggled under his arm with my legs across his lap. Glancing down, I saw my skirt had ridden up and the little bulge in my panties was on full display. With false modesty, I tried to press my thighs together to hide it, but to no avail.

"That's better, isn't it?" Daddy said, stroking my cheek with his large hand. "My sweet little princess would rather be safe in her Daddy's arms, wouldn't she?"

I nodded as his thumb traced across my lips. Does he want me kiss it? Or suck it? Usually at this point in the scenario, I'd find myself pinned down under Daddy's weight, or tied to the bed, or both, as he punished his bratty daughter with a good, hard fuck. Most men who'd picked this particular setting for date night liked it rough and they liked it quick; they'd slap me around then bend me over and take me. Not this guy, it seemed. After spanking the fight out of me, he had turned unusually tender.

Looking him in the eye, I kissed his thumb and he paused its movement across my lips. Slowly, I circled my tongue around his thumb. I held his forearm with both hands, enjoying my first caress of the hairy, well-muscled limb, then guided his thumb between my lips. My gaze never left Daddy's eyes as I eagerly sucked on his thumb.

"Baby, you're so beautiful," Daddy whispered. He withdrew his thumb from my reluctant mouth and leaned forward to kiss me. He was clumsy at first and his beard chafed on my softer skin, despite his best efforts to be gentle. It didn't take us long to get in sync, though, and soon I had my arms around his neck, pulling him closer as his tongue push deeper into my mouth.

Meanwhile, his hands were further exploring my body, namely between my thighs. He found that spot between my balls and my hole and gently rubbed it through the lace of my panties. I shivered with delight. His fingertip drew a line across the lace, between my balls and up the length of my cock, stopping when it reached the damp patch at the top. He peeled down my panties and let my cock spring free. His big, warm hand wrapped firmly around the shaft, covering my cock completely. I sucked at his tongue and nibbled on his bottom lip to let him know he was making the right moves.

Daddy's fist stroked my cock as we continued to kiss. I was leaking all over his fingers. Suddenly I was acutely aware of his jeans against my bare ass and wriggled my hips, grinding in a rhythmic motion, to feel the tough denim rub against my exposed hole. Moaning softly, I found myself temporarily disappointed when he pulled out of the kiss and released my cock. I grabbed his hand and licked off the pre-cum I'd left, savouring its sticky sweetness.

"You know what would make Daddy really happy, baby?" he said, settling back into the couch. I followed his eyes to his crotch and understood what was expected of me.

I placed my hand on the large bulge in his jeans. He closed his eyes as I rubbed him, the heat of him warming my hand immediately. Kneeling next to him, I leaned over and nuzzled my face against the denim. I breathed deeply and ran my nose around the outline of his shaft. God he smelled hot. Slightly sweaty, slightly funky. The perfect manly scent.

"That's it, baby," Daddy said, as I undid his belt, the button on his jeans, and finally the zipper on the fly. I tucked my fingers inside the fold of his boxers and pulled out his cock. Up close, Daddy's cock was bigger than I expected. It wasn't that it was long. It was above average, but really only slightly longer than mine. But it was thick. My hand couldn't reach all the way around. I gazed at it in awe for a moment.

"You like Daddy's cock, sweetheart?"

I nodded.

"Say it."

I looked at him. "I like your cock, Daddy."

He smiled and stroked my cheek. "Now show me."

I took him in my mouth, just the fat head at first, rolling back his foreskin and getting a good taste of his thick pre-cum. I focused on the head, in part because it felt so good, but mostly because I was worried that's all I'd be able to fit in my mouth. I had to switch to using two hands to stroke up and down his shaft, he was so big.

Leaning back even further, he slid his jeans down and let them fall around his ankles, and spread his legs to let me have full access. In turn I had to lean further forward to better explore the thick curly hair that grew around his cock and covered his sack. I licked his big, hairy balls and felt myself become intoxicated with that sweaty musk.

My ass was now poking right up in the air, a fact that Daddy did not let go unnoticed. I could feel his hand slip under my skirt and go straight for the crack between my plump cheeks. His finger eased aside my g-string and probed at my hole. He must have licked it first because it slid right in with just the merest hint of resistance. I groaned and pushed back, letting him know I wanted him to go deeper.

"Ooh, baby likes that, does she?" he teased. "You think you are ready to handle something a little bigger, sweetie?"

A flash of anxiety must have appeared on my face as I looked up from his cock.

"Don't worry," he smiled. "Come on, let's get you into the bedroom where you'll be more comfortable."

He stood up, removing his shirt and kicking off his jeans and shoes while I slipped out of my jacket and heels. Standing there, now naked, he was more attractive than I'd given him credit for. He wasn't fat; he was just big all over. Like his cock, his arms and legs and torso were thick, not to mention muscled and hairy. Even his face was starting to persuade me of a certain rugged handsomeness. When I stood up, he surprised me by picking me up, one arm under my knees, the other around my waist. I quickly clasped my hands around his neck to hold on and he carried me with ease into the bedroom.

Soon we were lying on the bed and kissing again, me on my back, him on his side, his hands fully exploring my body while mine caressed his fat cock. He teased and pinched my nipples under my shirt. He clutched my ass and massaged my cock. He licked my ears and bit my neck. I felt so small and delicate next to him, his rough hands and coarse hair making my soft, smooth skin tingle with every touch.

I closed my eyes and felt his kiss once more. I sensed he'd reached for the lube I'd retrieved from the bedside drawer and soon felt the cool liquid on my hands as they continued to stroke his cock. He slid an arm under my knees and lifted them up onto my chest and then I felt the slight chill of the lube dripping into the crack of my ass. I still had my panties on, so he again slid his finger under the g-string and massaged the lube deep into my hole.

"Are you ready, baby?"

"Yes, Daddy."

I feel the fat head of his cock enter my tight hole. I try to relax but, despite all the lube, the intense sensation still rides that fine line between pain and pleasure.

"Look at me, baby," he says, his arm returning to under my knees. He's basically cuddling me now, one arm under my head and wrapping around my shoulders, the other on top, across my thighs, pinning my knees to my chest. I look at him and feel his cock push deeper inside me. He kisses me and the pain subsides, suddenly it's all the pure rush of pleasure.

He fucks me in this sideways position, picking up speed and filling me with the full length of his fat cock until I can feel his balls slapping against my ass. I feel him tense up, his grip on me tightening, crushing me with his immense strength. His grunts grow louder and louder as his cock pounds harder and harder into my ass. His arms clench me as if he's trying to squeeze me in half. His thrusts stop, his cock buried inside me as deep as it can possibly go. His cum fills me up.

I can't move, trapped in his strong arms, and I can barely breath, but I don't care. I'm safe in Daddy's arms.

AmySissy96
AmySissy96
103 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
ColonelinguistColonelinguist8 months ago

I loved how quickly you arrived at the pure eroticism of this story Amy. Your description of Daddy’s extra thick cock made my mouth dry!

I’m On to chapter 2.

LannaLaceLannaLaceabout 1 year ago

Very well written! Well done! Will definitely be reading more of Amy’s date night experiences!

AnonymousAnonymousover 2 years ago

Nice little story with a lot of amunition for subsequent offerings. The sex is consensual and as expected by our heroine.

Share this Story

Similar Stories

Neighbors Sissy Son Training the boy nextdoor to be a fucktoy cumslut!in Transgender & Crossdressers
Seven Years as a Wife Man is blackmailed into being a wife.in Transgender & Crossdressers
Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
Full Scholarship Naive college kid tries to make ends meet, gets in deep.in Transgender & Crossdressers
"Sissified": 12 Days of Sissy-mas Straight man is turned into a submissive sissy by...in Transgender & Crossdressers
More Stories