Trying To Become Daddy's Little Halloween Princess

Started by Burak Deniz · 0 Replies
Posted: 2 yrs
I was always envious of the pretty, sexy silky clothes my three older sisters got to wear, and even during early childhood found the laundry hamper to be my favorite play pen as I could wallow in the feel and smells of their discarded intimate underthings. Not only did I sniff and fondle their underwear, but in the privacy of the bathroom, I would try on my sisters' bras, panties, and slips and prance and pose in front of the mirror, causing my little willie to get so hard it would poke out from under their tiny little bikinis and thongs.

I was the youngest of the family, and my older sisters enjoyed "babying" me as a child. They sort of treated me like a doll, dressing me up, playing with me. I have always been petite for a boy, small boned, and instead of ever being called "handsome," I would frequently hear people calling me "cute" or even "adorable." I have naturally long eyelashes and blue eyes. I love my blonde hair, and have always hated to have it cut, so I wear it long, past my shoulders. Particularly when people come at me from behind, I am often mistaken for a girl, maybe because, despite being a boy I actually have a shapely bottom that from behind definitely makes me look like I have a feminine figure.

Often, I thought of myself as just "one of the girls," along with my sisters. I always preferred traditionally girly activities and never went in for rough-housing or sports. There was only one Man of the House in our home--Daddy. My sisters always seemed to vie for Daddy's attention. He is a big, strong handsome and charismatic man. My sisters all had crushes on him and, truth be told, I did as well, I was as jealous of his attention as the other girls.

I had always flirted a bit with my father in the same way my sisters did. We would all try to snuggle in his lap at the same time or hang on his shoulders and arms when he was shirtless in the house or at the beach or swimming pool. My sisters often walked around the house just in little panties and bras or in see-through nighties, and I could see them sort of competing with each other to see who could get Daddy's eyes to follow them. I was at a disadvantage because I wasn't allowed to wear girl panties or nighties. My only opportunity to win Daddy over came on Halloween.

Halloween had always been a sort of a liberating holiday for me, allowing me to embrace my alter ego, and in a significant way it became my earliest entry point into cross-dressing and in the exploration of my sexual identity. Every Halloween for as long as I can remember, I chose to dress as an effeminate character, usually, a Disney princess, the Little Mermaid or Pocahontas, and my older sisters would put make up on me and make me look beautiful. Before we would go out trick-or-treating, we would always do a little preview fashion show for Daddy, and I could see from early on that his eyes would brighten when he would see me dressed in my girly costumes, and I loved prancing and dancing for him.

My relationship with Daddy changed one night when I came home late from a Halloween party when I just turned 18. On this particular Halloween, I had dressed as Princess Jasmine from Aladdin. I wore a beautiful, translucent light blue harem pants and halter set that exposed my midriff and back, a matching pair of high heels, bangles on my wrists and an anklet with little bells around my ankle, a necklace and dangling earrings. Before putting on the costume I had showered and put on body lotion that had little sparkles and a lot of perfume. I had put on blue eye shadow, which really brought out the blue in my eyes, red lipstick, and I had blown-dried my long hair so that it cascaded down my shoulder in waves. Of course, I had also shaved my legs and waxed all my body hair and carefully tucked my male "equipment" under my crotch, held in place by a tight, spandex thong that was clearly visible through the harem pants.

All the kids at the party had agreed ahead of time to try to swipe alcohol from our parents' stocks, so we had a wide an weird variety of spirits, wines, and beers. The party was in one of the kid's basements who had cool parents who stayed upstairs and ignored us. The basement was lit only with "black lights" the kind that keep it dark but make your teeth look real white and picked up the sparkles from my body lotion. Music was pounding, so you couldn't really talk and everyone just danced on the dance floor, not really couple dancing so much as everyone dancing with everyone. It was dark and steamy and a lot of us were pressed together.

I like to dance and my body really flows with the music. With the harem costume, I was doing a lot of hip swiveling and belly dance kinds of moves. I felt like Shakira on the dance floor. I think I must have looked pretty sexy because a lot of kids wanted to touch me and sort of dance with me, but to my surprise more boys danced with me than girls. What really made me feel sexy was that I could feel a couple of the boys press their hard cocks against my butt as I swiveled my hips. Everyone there knew me and knew that I was a dude, but it was Halloween, it was dark and crowded, we were drunk, and I guess everyone was pretty horny, including me. I was horny, and I did think a lot of the girls there looked great, but what got me really excited was knowing that I was turning on some of the guys, and I really enjoyed flirting with them and seeing -- and feeling -- their reactions.

One of the bigger guys, Joey, who is a football player and whose "costume" was his football uniform was the only one who tried to make fun of me, calling me a fag and that sort of thing. But I was too drunk and having too much fun to care, and just flirted with him all the more, batting my eyes at him, making little kissy faces at him. As the evening continued I noticed he stopped calling me names, but that he kept looking at me whenever he could. When I finally left the party, I put on an overcoat and started walking back to my house. I didn't notice at first, but became aware that somebody was following me. I looked over my shoulder and saw it was Joey. It was cold, but I decided to take off my coat, so walking behind me, Joey would see my runway model strut, in my high heels, harem pants, and thong. I made sure with every step that my ass was really swaying.

I got to the front door of my house and was just finding the key to the door when Joey came up swiftly behind me. Suddenly he crushed me against the door, pressing his body hard against me. "Bitch," he grunted in my ear as he started humping and thrusting against my ass as his hands grabbed at my nonexistent breasts. He was banging up against me and slamming me into the front door. He jammed me up against the door and pulled down his football pants and my harem pants so his hard penis was rubbing against the thong that went up the crevice of my buttocks. As he thrust against me, he banged me into the front door. Just then, the door opened with Daddy standing in the doorway. I tumbled into Daddy with Joey falling right behind me.

All three of us were pretty shocked. Daddy looked down with an expression that looked like a mix of surprise and anger. Joey and I were at Daddy's feet, both of us with our pants around our knees with Joey on top of me. Joey, rolled off me, pulled his pants up, and ran away. Daddy pulled me all the way into the house and closed the door. I was shaking and disheveled. Daddy held me by the shoulders and looked down at me. I could see a change in his expression. The look of anger was gone. I was relieved; he was not angry with me. I looked up at him, and our eyes just locked on each other for a bit. We had never looked into each others eyes before, not like this at least. My hair had fallen across my face, and he brushed it back. Then, he did something unexpected. He hugged me, just held me protectively in his strong arms and let me feel his warmth and strength.

My parents had also been out at a Halloween party. Mom was passed out upstairs and Daddy smelled of whiskey and was still in his pirate's costume. He was wearing one of those "puffy shirt" pirate blouses that has a scooping neckline, so when he hugged me he brought my face into his chest and his thick chest hair sort of tickled my face.

"You look pretty shaken up, Timmy. Maybe you should have one of these too." He was having a nightcap. So, he got another glass and poured me some of his Scotch.

He led me to the sofa in the family room. We sipped our drinks. The house was quiet. One of my sisters was already off to college and the other two had sleepovers at friends houses that were also having Halloween parties. So, it was basically just Daddy and me.

"Are you okay? Was that boy hurting you?"

"I'm okay, he's just sort of a big stupid lug who I was teasing a bit."

"Teasing big stupid lugs can get you into trouble."

I gave him a little smile. "Yeah, I should be more careful." We sat quietly sipping our Scotch. I noticed Daddy looking at me. Then, we locked eyes again.

"You make me feel like a big stupid lug sometimes," Daddy said, almost in a whisper. I looked down. There was another pause. "I feel like you tease me a little bit, too, sometimes."

I looked up and gave Daddy a little smile.

"But I like it when you tease me." We sat looking at each other, sipping our drinks. "You look so beautiful tonight, Timmy. It makes me want to call you Kimmy instead."

I smiled again.

"You are so pretty, Kimmy. Why is it that you are such a pretty little princess?"

"You make me feel pretty, Daddy." I looked at Daddy, but this time I batted my eyes, parted my lips. I wanted to look sexy.

He held my gaze. Then, Daddy got up, refilled our glasses, and put on some Middle Eastern belly dance music. "This won't wake up Mommy. She's out cold." He took pillows from the sofa, threw them on the floor, and made himself comfortable on the pillows, like the Sheikh of Araby.

"Dance for Daddy," he said. "Be my secret harem girl tonight, Kimmy."

I stood. I felt the music first in my fingertips. The music moved through my fingers and my hands and wrists began snaking sensuously in the air. My shoulders responded next and soon my long blond hair was swaying as well. Then the music moved into the core of my being and took over my hips. As the music swelled, my hips gyrated. My eyes were mostly closed, but I would take little glances of Daddy, looking like a grand pirate, sprawled at my feet, enjoying the show.

I swirled and swirled, my hips swiveling, and though a virgin, the music, the drink, the evening, brought out a sensuality deep in my soul and made me feel as though I was making love. I ground my hips to the music feeling like a woman being driven to ecstasy by the thrusting into the center of her body of a hard, powerful cock.

I had been totally lost in the music and the response of my body. I hadn't been aware that Daddy had unbuckled his pants and was stroking his large and growing cock. I straddled him, dancing over him. Then he got to his knees and put his hands on my swiveling hips. My own penis started hardening, which was not good because I had it tucked away as best I could. I changed tempo, slowing my hips, and taking Daddy's head in my hands. His hands, meanwhile stroked my back and then came down and he cupped my derriere. I lost my balance and sort of fell onto the sofa. Daddy rose up. He pulled off his pirate shirt, kicked off his pants, and stood in front of me, naked.

He was gorgeous, a passionately hungry expression on his handsome face, broad shoulders, hairy chest, bulging biceps, and a ramrod cock sticking up straight and tall. I had waited so long. I wanted him so much.

"Do you want to be Daddy's special little princess?"

"Yes, Daddy."

"Promise not to tell Mommy?"

"Yes, Daddy."

"Would you like me to call you Kimmy instead of Timmy when we're alone together?"

"Oh, yes, Daddy, I would love that."

"Okay, Kimmy. I think you are beautiful and sensual and I want to help you realize your true femininity and sexuality."

Daddy looked deeply into my eyes, pulled me up to my feet and enveloped me in his big strong arms. he tipped my head back and kissed me on the lips. The rush of excitement I felt was unbelievable. I parted my lips and Daddy's tongue moved deliciously in my mouth. I was still in my harem-girl outfit. My Daddy, My Master was naked against me, his masculinity pressing hard against me. i felt his hands on my back and then cupping my bottom. My knees were so weak, I was dizzy just holding on to him as he continued to probe my mouth with his tongue.

I wish the kiss could have lasted forever. As Daddy's tongue penetrated my mouth he ran his hands over my body, my hair, down my back, I felt his middle finger follow the line of my thong from the waist band down into the crack of my as his other fingers fondled my bottom cheeks. Daddy's other hand came under the front of my halter top. He squeezed and played with one of my nipples, making me feel like I had real womanly breasts. The sensation was intoxicating.

Before long, Daddy and I were back on the couch, necking, kissing, utterly lost in the sensations of each others touch of the exploration of our mouths, our bodies. I kissed his neck, almost leaving a mark but he pushed me lower and I sucked on his chest instead.I could feel his thumping heartbeat through his barrel chest as I the mark from my sucking right over his heart. I could feel the pressure of Daddy's hands pushing my shoulders, guiding me lower, down his torso, tracing the line of hair from his naval, and then finding the hardness of his cock on my face, and then the softness of his cockhead in my mouth as I swirled my tongue around his tip. I massaged Daddy's ass and the back of his thighs as I sucked on his cock, feeling his muscles with my hands and his hardness with my mouth.

I still had a little tube of the sparkly body lotion in my purse. I squeezed the lotion onto my hands, warmed it up a bit and then lathered the lotion on Daddy's cock, pumping it so that it looked like it would explode. Daddy pulled down my harem pants and my thong. He took the lotion and put some in his hand, too. But instead of going for my penis, Daddy's lotioned middle finger went for my tight, puckered boy pussy. As I stroked his cock Daddy was working his big finger in and out of my bottom, getting me to move in rhythm to the pumping of his hand as it penetrated me.

Daddy put me into a face down position on the sofa, put some pillows under me so that my bottom was sort of sticking up in the air, and positioned himself behind and on top of me. I quivered and wiggled my pretty little bum in anticipation.

Daddy leaned down and whispered in my ear. "Does baby Kimmy want Daddy's big hard cock in her pretty little pussy?" Daddy's finger was now deep in my boy pussy.

"Yes, Daddy. I'm all yours."

"This might hurt, baby."

"Hurt me, Daddy."

Daddy then got forceful, took complete control. He grabbed my wrists with one hand and held them stretched over my head. He kissed me hard between my neck and shoulder, actually biting me. Simultaneously he pulled his other hand out of my pussy hole and then I could feel the real thing, Daddy's big cock, penetrating me. Yes, it hurt, but in the most glorious way, and soon Daddy and I were moving completely in sync."

"Oh, Daddy, yes, oh, my love, my Daddy," I murmured as Daddy groaned and thrusted into me.

Daddy's thrusts built to a crescendo and he climaxed deep inside me, and then I felt his full weight on top of me, felt the slick sweat of our bodies, and felt his heavy breathing. We stayed like that for several minutes, but then I got afraid that we Mommy would wake up in the morning and find us this way on the sofa.

So I wiggled out from under Daddy, and woke him with a kiss.

"Thank you, Daddy, you changed me from an ugly little boy frog into a beautiful girl Princess."

He gave me a dreamy look. "Yes, Kimmy, you will be my sexy little Princess and I'll make sure we will find ways not to have to wait until Halloween for Daddy to make love to you again."

Proudly signed,

Willing wimp
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