The Ladyboy & Her DadbyGolbard©
I had always been fascinated with women's clothing. As long as I can remember I've always loved the way it looked. And forever was I curious with the way it looked on a hot girl, the way it moved, how it stretched over every curve, and the way it must feel. I was mesmerized with the effect a beautiful woman had over every guy in a room. How could a pair of pretty eyes capture the gaze of every man within sight? Very soon, I was about to find out.
I suppose the first time that I ever gathered the courage to try on women's clothing was after school one day, when I was 18, during my senior year of high school. My parents never came home within four hours of school being out so finally I took advantage of my timely situation and that day my fears were overcome.
Opening the door to my parents bedroom I went straight for my mother's dresser. Upon opening the top drawer I found all her lingerie. Panties, nylons, bras, girdle's, you name it she had it. At forty years of age, she had the body that any woman would die for. My own body was rather small. At a little over 5'6 I weighed a measly 120 pounds. For a guy this was bad, but for a woman, this was ideal.
After stripping naked I pulled out a pair of black nylons and laid on my parents bed and becan to roll them on. I had already shaved what little hair I had on my body and the feeling of them stretching up my smooth calf and over my knee was too much, and I instantly became aroused. Once I had finished putting them on I followed with a pair of matching panties. A bulge was instantly noticeable which was fixed by folding my penis between my legs. After strapping the clips to the lacey top of my nylons I rummaged through her drawer some more. I stumbled upon a pair of latex bust enhancers in the back of the drawer. After putting them on inside a black bra, I put on a very thin black, low cut shirt which showed the bra and created the illusion that I had very nice C cup breasts.
I went into my parents bathroom and fumbled around with some of my mother's makeup. After toying around for around a half hour I managed to get one of her wavy jet black hair pieces on and applied a minimal amount of makeup. Looking into the mirror I was surprised with the result. I found a pretty young girl staring back at me and surprised I smiled at myself. I went to their closet and picked out the sexiest high heels I could find. After putting them on I walked around in from of their huge dresser mirror. I didn't have much when it came to curves, but I found that if I arched my legs and shifted my weight, it created the illusion that I had shapely hips. Lying on the bed looking at my self I couldn't help but notice how great I looked. My small feet fit nicely into the heels and going up I stared at the womanly long pair of beautifully toned and silky smooth legs.
Posing for my self for what seemed to be a short time I looked over at the clock and realized that either of my parents could be home at any minute. Thankfully I removed everything and got it all back to their original places before they got home.
Three years after this first attempt, I had come a long way. I had grown out my own hair which was black just like my mother's. My skin was no longer white but a nice tanned shade. My already high voice now sounded higher pitched and had a girly tone within it as I practiced talking and eventually I sounded just as any woman would. I had been on horomones which helped with my voice and my body had very nice curves and full breasts. My parents by now knew of what I was and were very supportive of my choice which was the biggest jump to hurdle. Over this time I had gotten very good with the makeup and hair and by the time I was done, I was no longer staring at a cute girl, but a beautiful, full breasted woman.
One day, when I was visiting my parents from college I found myself back in the room where it all started. I stood in front of that same mirror and thought I'd relive that first experience. I was dressed in a short leather skirt and open toed heels which laced all the way up to my knee. Along with a red, skin tight, stretchy sweater and the best looking hair and makeup job yet, I looked undoubtedly like a young woman. No second guessing was needed as I strutted around arching my back and swung my hips back and forth.
After I had finished fluffing my wavy black hair out over my shoulders I turned and as I looked up I saw my father sitting on the edge of the bed just staring at me.
"You know," he started, "I didn't know what to think when I heard of what my you began to do. But now I can't help but love the beautiful thing that has turned out." At this he stood up and walked over to me and wrapped his arms around me as I stared up into his eyes.
I instantly knew his intentions when he spoke those words but I had never thought of being with my own father. But now as I looked into my father's eyes with his big arms wrapped around me, some feminine need stirred inside me and it felt strangely right.
He pulled me towards him and our lips met, my soft moist lips meeting with his sent shudders through me. He grabbed both of my ass cheeks and mashed them into each other and towards him as our tongues played with each other's mouth. He exhaled against me and I breathed in his hot breath as we explored each other's mouths. I felt his cock start hardening as it pressed against my thigh. I put a hand over the straining head of it and squeezed it through the fabric of his pants. As I massaged his dick head he gasped breaking our hot wet kiss. He then leaned down brushed my hair aside with his hand and kissed up and down my neck. I leaned into him where I gently whispered in his ear.
"We can't kiss forever daddy." I stepped back unbuttoning his shirt, and I rubbed my small hands all over his thick and hairy muscled chest. After that I lowered myself to the ground and undid his belt buckle and unbuttoned and unzipped his pants. I pulled them to the ground which left only his boxers and one hell of a boner waiting to be set free. I pulled the back of his boxers over his butt and then from the front pulled them down the rest of the way. His eight inch cock sprung free and jutted out, nice and thick. I looked up at him and smiled devilishly as I extended my tongue and licked the underside of his cock, starting from the back all the way to the front. Before my tongue left the tip I mashed my whole mouth over his swollen dick all the way down. I squeezed his naked ass and rubbed my hands up and down his chiseled thighs. I could feel his pubic hair against my face as I pushed my face as far down as I could.
I continued sucking his dick for several minutes before withdrawing, I gripped it and squeezed up forcing the precum out the tip. I licked it and then closed my mouth around his head and sucked hard as I jacked him off with my hand. It wasn't long before I heard loud moans and he started shouting.
"Oh fuck yeah, my little bitch is sucking her daddy's cock!"
He backed off and his dick flopped out of my mouth. "I'm saving this load for another hole. Soon you'll have cum leaking out of your hot ass. Go lay on the bed." I obeyed and he came over and straddled me. He kissed me and then reached down and pulled my panties off. He leaned over me and we kissed for a minute before he leaned back and rolled me over with his strong hands. He reached over to the nightstand and pulled out a bottle of lube. Pulling me up to my knees with my ass being presented to his face he stuck his tongue against my hole and licked up and down. I squealed in ecstasy as I felt his tongue slip into my puckered hole for a moment. Twisting the cap off it left a rounded tip which he inserted into my hole and squeezed. After pulling it out several drops ran out of my asshole which he used to smear around the area with his finger.
After playing with my pussy butt for several minutes, inserting and stretching my hole with his fingers he stopped. He brought one leg up, leaving the other down on the bed as he began to mount me. I felt the tip of his masculine dick prod into me and after a couple seconds of constant pressure, the head slid in suddenly and I shuddered with the satisfaction that I felt. My hole had been worked enough so that he just slowly started pushing in. Upon burying his dick in to his balls I felt so full and complete. He withdrew and then slid back in a moment later resting his cock inside me for a moment so my ass could get used to a big dick being shoved up there.
Once my ass was used to being filled with my father's rod he started bucking away giving no mercy. He fucked me hard and I screamed in excitement. Withdrawing, he flipped me over to my back again and climbed on top of me. I wrapped my legs around his waist with my heels still laced up to my knees as I felt his tool find its mark and once again he plunged in and started fucking away.
"Oh daddy yes!" I screamed as he hammered away at my tender hole. Half moaning half screaming I blurted out, "Daddy's gonna cum in his daughters ass and fill it up with his cum, aren't you daddy?" He closed his eyes and continued to move in and out of me while he spoke.
"Fuck yeah honey, daddy's gonna make this the best day of your life, cuz I'm gonna cum up you and fill you up with my load."
Only moments after he spoke, he began fucking me like an animal. "Oh God, here it comes, I'm CUMMING!" he yelled as he buried his dick in me one last time. I could feel his dick pulsate as shot after shot of hot cum squirted into me.
Still laying on top of me with his dick in my ass he ran a hand through my hair and smiled at me. I smiled back at him and we leaned together for a kiss. As we broke, he whispered to me, "You know this can't be the last time right?" I just smiled and pulled him in deeper with my legs as we began to kiss again.