CW: this story is about gender fuckery and fucking your way to gender euphoria one problematic literary costume at a time. READ AT YOUR OWN RISK THIS IS VERY EXPLICIT and here take some theme music. Piece originally in print circla 2014 I think
Her tie flaps between her breasts as she starts to bounce; I want to close my eyes but can’t take my eyes off of her. Her glasses are crooked and her mascara is smeared around her large round eyes. I’ve never seen her this way.
I have never been this way.
It started with an invitation to a costume party. She has been dressing me in bits of ladyness for months. Sly pretty jewelry, silken underthings and touches of mascara. She likes me wearing eyeliner and the occasional pair of panties. She makes me feel pretty. I am never able to ask her to make me her girl.
When the invitation arrived she knew right away what to go as.
“We’re going as Lolita and Humbert.”
I was glad we had a few months to prepare. She left it to me to find my own outfit. I decided to outfit myself from the skin out. I found a pair of delicate and beautiful ivory silk tap pants to wear over my briefs, I tried wearing just the tap pants but found that the silk made me half hard and that ruined the line of my skirt.
Finally after much deliberation I settled on a vintage brown woolen skirt, oxford shoes and white ankle socks. I wore the blouse she liked, an ivory midi blouse with a tawny sweater. I learned to curl my hair into sausage curls.
She didn’t let me see her beforehand.
When she came to pick me up I wanted to take her right there. She wore a dapper little gray suit with a scarlet tie printed with tiny fleur-de-lis, her shirt was crisp and cream colored with a discreet tonal stripe. I could see the shape of her little round potbelly, she doffed her hat at me and I was through.
I recall that once I put on my heart shaped sunglasses our friends got it immediately. At one point she cornered me and held me against the wall, whispering in my ear.
“Lo-lee-ta.”
She lowered her voice to a throaty rapacious purr, rasped her teeth against my neck and I held her by her soft bottom. My cock was so hard it was sore. We had to leave.
We broke character, no I should be honest I broke character when she lingered to allow some friends of ours to fondle her tweedy rear end. I swept her up and onto my shoulder, so as to offer everyone in our path swats at her plump jiggling butt.
She slapped my hands when I tried to touch her as she drove.
“Don’t behave inappropriately in the car.”
Her clipped short tone felt masculine and put me right back into character. I giggled and slouched in my seat and reached into my little purse for some bubblegum. I watched her mouth tighten out of the corner of my eye; every time I snapped it or made some other noise with it she winced.
When she held her hand out I let the gum drop and rolled my eyes.
“Really Hum?”
She grunted, wadded up the gum in a piece of paper fished from her pocket and lit a cigarette.
“Really Lo?”
Her voice was low and husky, I felt my cock twitch and reached to turn on the radio. I found a pop station and turned it up loud, singing and tossing my head. After a couple of minutes of my warbling about grinding she turned the radio off.
“Must all your music be so vulgar? That is hardly the kind of thing a young lady should be singing about, grinding. What was that lovely song you were singing the other day?”
She began to hum, low and deep in her throat. I didn’t recognize the song but when she glanced at me and winked I melted.
As we cruised into the last ten mile stretch before home I started to fidget, I played with my skirt, the radio, tried to snatch her cigarette. She swatted my hands when I unbuckled my seatbelt a block away from home and tried to plant my face in her crotch.
“Dolores! You stop that immediately and behave yourself.”
She started rumbling about a spanking and I was vibrating with happiness. She pulled into the driveway, trotted around the car and spoke in a tight hard whisper.
“Come along young lady.”
There was a masculine menace in her voice that chilled me and I felt my balls contract slightly and I ducked my head. She took my arm like a gentleman and led me inside where she took my coat and sat me on the couch while she poured two fingers of bourbon and drank it straight away.
“Lolita, do you have anything to say for yourself?”
She turned to look at me,arms crossed, a line between her brows. I straightened my skirt and gave her my biggest, sweetest smile.
“Well, the canapes were good and the punch was good but did you see what Lorraine had on? You could see all the way to Cleveland in that get up.”
I prattled about the music, gossiped about our hosts screwing in the bathroom.
“It was positively indecent. Tell me Hum, do you think Ann is attractive?”
The look in her eyes made the bottoms of my feet still clad in the frilly socks tingle, I was still smiling and enthralled by her put upon look.
“Well Lolita, I’m sure she is attractive in her way. If one is attracted to dodu petit chou. There is something to that kind of roundness that speaks of Hedonism and fertility. She has a certain charm I suppose. I know men who go mad for that kind of rosy cheeked, buxom sex pot type.”
I narrowed my eyes, rose and looked at myself and her in the mirror over the mantle. I found my cherry flavored lip gloss and reapplied it carefully before turning and hurling the little thing at her.
“Why don’t you go touch her then.”
The lip gloss pinged off of her chest and she let it drop. Perhaps I went too far, I froze in place with my sweet shiny lips parted. She calmly put her glass down on the side table, bent and picked up the tube of lip gloss. She studied it for a long moment and eased herself down onto the couch.
“Come. Here.”
Trembling I moved over and quick as a snake she grabbed the front of my blouse and pulled until I was forced down so we could be eye to eye.
“No need to be nasty Lo. Let’s us make up.”
I smiled at her again, curls hanging in my face. She kissed my cheek.
“But first, punishment.”
She used steady pressure until I was positioned. I lay across her lap pink and trembling.
Her movements were so careful and precise, she lifted the hem of my skirt and chuckled. Her voice even and measured.
“See through Lo? What a nasty, filthy girl you are.”
I made a noise I didn’t know I could make, a wavering whimper. I felt her run her fingers over the silky tap pamts then she carefully edged them down just under my ass.
“Count.”
How she made her small soft hand so big and hard I will never know. The first solid wallop took me by surprise and I gasped.
“One.”
The next landed on the other cheek, hard enough to bring tears to my eyes and heat to my face.
“Two.”
“Don’t cry my love.”
She cooed, gave me two light taps and then two that took my breath. I couldn’t count anymore, it was the first time she spanked me and I was breathless. She had a knack for finding the tenderest spot on my butt and rubbing it with butterfly sweet fingers and then wham.
“Ow, ow nine.”
I squirmed, sniffling and trying not to cry. The silky slide of my panties between my cock and her tweedy pants was driving me insane, my ass felt like it was burning and she was humming again, that low vibrational hum that somehow transmitted itself right into my brain.
“No more, no more please.”
She was rubbing my hurt, I could hear her smile.
“Oh, low-lee-ta. One more and then we make up. Ready?”
I tried to catch my breath and failed. I mewled.
“Yes Sir.”
I felt her wind up and I tensed a little, she gave one buttock a light glancing slap and followed it with a vicious pinch on the other side that made me grind against her, moaning through my tears.
She resumed stroking me, rubbing the backs of my thighs, dipping her fingers between my cheeks to touch my asshole lightly.
“Oh, like that do we?”
“Yes.”
I was embarrassed, I couldn’t stop moving my hips and felt like I was going to shoot my load at any second.
“I bet if I left the room you would touch yourself wouldn’t you my little trollop?”
I pressed my lips together, fighting the answer until he pinched me again.
“Answer me.”
“Yes, yes sir.”
She patted my back.
“Get up, fix your panties and your skirt.”
I did as I was told, gingerly standing and turning my back to try and regain my composure. I eased my panties up and heard her rustling about.
“Don’t turn around.”
Her tone changed, she lost her smooth Humbert and I heard the shift to Daddy. I could hear her rummaging in her bag for something. My cock strained against my panties and I folded my hands together and bowed my head, trying to will it to go at least a little soft.
“You may turn around.”
I turned and she sat there in the button up shirt and her tie thrown over one shoulder and her magnificent gleaming black cock jutting from her crotch. I lost a little time, I felt Girl descend from the heavens and into my entire self.
She gestured to me and I walked over and knelt between her legs. She rubbed tears off of my cheek and onto her cock.
“You want a reward?”
She scooted her ass forward and put her hands behind her head.
“Yes Daddy.”
She found my girl voice.
My voice may have been small but my mouth was big. I devoured her cock. I knew her cock as well as I knew my own, I knew how to jiggle the base against her clit until she couldn’t watch the length of it disappear into my greedy mouth.
Her hand landed in my curls and knotted there, her hips jerked and she closed her eyes. She tilted her head back, fucking my face in short strokes until she pulled my hair until our eyes met.
“That’s it girl, you suck Daddy’s cock.”
She pulled it out of my mouth, watching me lick the tip for a moment before she pushed my head back down slowly. I felt it tap the back of my throat and I took it, I took it all and she watched with her mouth open. My eyes turned up to hers, I had been practicing and she grinned.
“Filthy slut. Only bad girls deep throat.”
She pulled it out again and looked at me, holding her cock with her other hand, jerking it rhythmically in my face.
“Are you ready?”
I swallowed.
“Yes Daddy, please fuck my face. Please. Let me show you I can do it.”
She pushed me away and stood up, she put her little hands on my face and stroked it gently.
“I’ll go easy.”
I didn’t want her to go easy and before she could ease her cock down my throat I dove on it. I held her by her thick quaking thighs and swallowed for all I was worth. She wrapped her hand around the base, grinding it into her clit as I slowed so she could watch the length of her cock disappear between my still pink stained wet lips.
“That’s it, make Daddy come.”
That was my cue, as she jerked her cock in my face I reached behind her and slid two fingers into her wet open cunt. I timed the slide of my fingers against her lips with the bucking of her hips, I tickled the very entrance and she bared her teeth at me..
I felt the orgasm move through her in waves and jammed my fingers all the way inside her the way she liked. She howled curses at me, her cunt squeezing my fingers in hard serious waves. When she relaxed a little I pulled my fingers out slowly and licked them.
“Did I do good Daddy?”
She reached down and petted my hair, putting my curls back one by one as she caught her breath.
“Good girl. Now go upstairs. I’ll be there in a minute.”
My cock had subsided enough that I could walk with some dignity out of the room and upstairs. She called after me.
“Leave the panties on.”
My step faltered but I was smiling. She was going to do her worst to me as I had offered the week before the party. Wanting to continue to be in her good graces I went upstairs and did as I was told immediately. When she was Daddy, there was a routine. I was to get into the state of undress she’d ordered and lay on the bed with my hands folded on my stomach and nine times out of ten my cock pointing due North.
While I lay waiting I heard her come upstairs and could smell cigar smoke, I curled my toes and tried to keep calm. When she walked in I looked up and my formerly calm cock throbbed and got so hard so fast it took my breath.
She stood in the doorway stripped of her harness, her shirt and her minimizing bra. She wore only the tie, her glasses and her hat at a jaunty angle. The cigar was clamped between her teeth and she puffed it hard to get good ash and walked over to tap it, the ash floated down and tickled my belly.
“Lay back girl.”
“Yes Daddy.”
When I was in a position she liked she got on the bed and straddled my hips. She reached between us and gently adjusted my cock to keep the elastic in my panties from stinging. She stroked it and smiled.
“Look that big ready cock. Is that for Daddy. You are such a little whore. I see what you’re good for.”
The smoke had roughened her voice and she leaned over to blow a cloud of it in my face. My eyes rolled for a second, I sunk further into girl.
“Yes sir. Thank you Daddy.”
She lowered herself bit by bit and pointed the cigar at me. It reeked to high heaven and the oily thick stink of it coated my mouth as I inhaled as much of it as I could.
“Open your eyes cunt.”
My eyes snapped open.
“Yes Daddy?”
She waited a beat, her gaze fixed on mine.
“You will not come until I tell you to, do you understand?”
I swallowed, I was not good at orgasm control.
“Yes Daddy I’ll try.”
She slapped me hard enough to make my whole face ache.
“If you fail you sleep on the floor girl. Understand?”
I swallowed and started to cry again.
“Yes Daddy, I promise Daddy.”
Deftly she tucked my hard cock back into my thin panties. She slid her sopping wet cunt slowly against my cock until the thin material was soaked. I moaned, I held still and ground my teeth as she did what she wanted. I closed my eyes, praying I could hold off.
“Open your fucking eyes.”
I did as told, I watched her roll her nipples between two fingers, still holding the cigar firmly between her teeth. Her head tipped back and the hat rolled away. She moved slowly, an evil grind that made me weep.
She murmured as she slid her hands down her belly and I watched her stroke her clit a few times, then she flickered her fingers over the head of my cock and I yelped. She smiled.
“Good girl, good girl, that’s my girl.”
That slow, wet movement wasn’t enough to put me over the edge and she knew that. My cock was so hard it hurt and she got wetter and wetter. I had my mouth closed tight again, my hands balled into fists at my sides. I wanted nothing more than to be inside her, when she rose slightly and began briskly rubbing her clit over the head of my cock I wailed.
At some point in my lust haze I had knotted my fists in my hair and was begging her, crying and quaking beneath her.
“Please Daddy, please Daddy, please Daddy please fuck me? Fuck me please? Please?”
She chuckled at me and patted my belly, the cigar had gone out and she climbed up my body to put it carefully into the ash tray. She positioned her slick gleaming cunt above my face and waggled her hips.
“You want to get fucked girl?”
I wanted anything, everything.
“Yes Daddy, please Daddy fuck me? Fuck me please?”
I watched her part her lips with two fingers and she dipped a finger inside, I could hear how wet she was. Her smell mixed cigar smell filled my nose and mouth. I was drooling; insensate with need.
She waited a long time, showing me what I needed. I yelped again when she moved off of my face, I almost grabbed at her.
“All right girl. Get your panties off and lay back down.”
I almost hurt myself in my haste. Wet silk does not come off easily around a swollen angry needy cock. I took a breath and slowed down, I got them down to my knees and looked at her.
“Please Daddy? Now please?”
“Get them the rest of the way off you stupid slut.”
The tears rolled down my cheeks unchecked, I almost lost my balance but managed to get the sodden panties off. I laid back down, panting.
She moved into position and took firm hold of my cock, twisting her wrist slightly just in case. She held it and looked at my face.
“What did you promise cunt?”
My breath caught in my throat and I felt like I was drowning in my own need, lost in it. I was completely under her control.
“Don’t come, I won’t come until you say.”
Satisfied with my answer she guided my cock inside her and sat still, watching my face. She held her muscles tight around my cock. I wanted to grab her plump hips and thrust into her until I passed out and she watched me fight it, watched me obey.
“Good girl. You just lay there until Daddy says.”
I moaned.
“Yes Daddy.”
I had to close my eyes, I couldn’t look at her and not come. She rolled her hips, adjusting herself and my whole body flushed. She ground slowly against me, rocking her hips in a terrifying rhythm, I needed more.
When she started to squeeze I almost lost it. The wet sweet rolling pressure made my eyes cross. It wasn’t enough to make me come but I got close, so close I bit the inside of my cheek and heard myself whispering.
“Don’t come, don’t come, don’t come. Daddy said, Daddy said, Daddy said.”
It was her turn to groan, she stilled until she was barely moving. She bent over and kissed me gently, whispering against my mouth.
“Ask.”
I keened, opened my eyes and stared at her in pure misery. My chest hurt, my hands shook and my entire world shrunk down to my aching girl cock and Daddy’s tight wet cunt.
“Ask me nicely cunt.”
It took every bit of will I could muster not to come, not to grab her and hold her down on my cock.
“Please fuck me until I come Daddy? I need it so bad.”
My whisper was thick with frustration, pain and tears. She straightened herself up, grabbed my hands and put them on her hips, she leaned forward and rose a bit before slamming her cunt down hard on me.
We howled.
She rode me hard, her nipple smacked me in the mouth as she gained momentum. Feral wailing, sublanguage roared out of me. It felt so good, the fight felt so good, I wanted so badly to keep my promise.
I had one way to get what I wanted. When she straightened up and started grinding and bouncing I opened my eyes to watch her. Her glasses sat crooked on her sweaty exuberant face, the tie flapped merrily between her breasts and her eyes behind her crooked glasses were huge and wild.
I reached between us and used the flat of my thumb against her big hard clit. She howled and stopped bouncing, moving her hips in short hard thrusts. I stroked slowly, watching her face. I had to concentrate to keep my rhythm, when she started to grin I stroked faster.
“That’s it, yeah. Yeah you fucking slut make Daddy come. Make Daddy come all over you filthy little cunt.”
On the last word her voice dragged and her mouth dropped open. She dropped her hips and tilted her pelvis, I stroked for all I was worth until I felt her cunt open slightly then clamp down around my cock in hard brutal contractions.
She pulled one nipple, her whole body bent forward, her back bowed and her little belly jiggled and heaved as she came. I was too distracted to lose it and come, I could feel her cunt moving and the new flood of wetness. I had made her squirt for only the third time.
In that moment my pride made me forget myself.
“You like that don’t you?
She made a garbled noise and slapped my hand away and got off of me. Her upper lip lifted, I cringed and she slapped me again. She got on her hands and knees, waving her magnificent ass at me.
“You think you’re special now girl? Try it.”
Cock in hand I positioned myself the way she liked. I shoved my cock into her, forcing it in deep, my hand on her belly to tilt her pelvis. We stayed like that for a moment before I lost my cool.
Growling and drooling I thrust into her hard, I felt something inside her move again and I think the tip of my cock was hitting her cervix. She was snarling at me, her voice went straight through me.
“So good, so fucking good. That’s it make Daddy come, you fuck your Daddy right. You fucking whore.”
Our bodies slapped together louder, I was howling and when she started to come again her torso dropped and I eased in that much deeper.
“Oh fuck, oh fuck, please please Daddy let me come, please let me come.”
Her silence in that moment made me want to throttle her, there were tears again I think as I begged incoherently, each stroke pushing me closer to punishment and sleeping alone on the floor.
When her orgasm subsided to arrhythmic flutters she laughed. She ground against me and I wailed, sobbing with breath I didn’t have to spare.
“Please, please Daddy please.”
I was wheezing and choking, I swiped tears and everything off of my face.
“Come.”
I reared back, holding her on my cock and grinding as the orgasm took me over. My thighs seized up and the soles of my feet burned, my ass burned from where she’d smacked it and when she reached back and dug her nails into the tender spot I started to come.
“Yes Daddy, yes Daddy fuck I’m coming I’m coming I’m coming.”
The world dissolved into red fireworks and my spine whipping out of my cock, my ears started ringing and as I came I sobbed harder. I felt like I was having a stroke and I never wanted it to end.
We collapsed when the last of my crushing orgasm dribbled out of my cock, I was so excited, so hard my cock stayed half hard inside her and we lay spooned in our wrecked bed.
Panting and dizzy I put my arm around her.
“Humbert, Daddy, Alicia I love you. Thank you Daddy. Thank you thank you.”
She laughed a little, I was still crying. When we could move she turned over onto her back and I laid my head on her belly, toying with her still sensitive and engorged clit until she pinched me.
“Stop that. I love you too. You’re welcome girl.”
Normally after something like that I would fall asleep. I laid with my ear to her belly, listening to the rumbles inside while she patted and untangled my ruined curls.
My crying subsided slowly and I wrapped my arms around her and rolled over, pulling her onto my chest. She kissed the underside of my chin gently.
“Are you okay baby?”
It took me a minute to answer.
“Yes, thank you for making me your girl. You’re the only one-”
The rest was lost to more tears. She cried when she saw me grinning like fool through my tears. We kissed and wept, we wept and laughed. When we stopped weeping, we slept.
Alicia made me her cocksucker. She made me a weeping girl. She helped me be a man.