Sissy Meets Daddy

I never noticed in the moment, but I had been a sissy my whole life. Growing up I was always the shortest boy, always the weakest, I never had a girlfriend, and I wasn't good at any sports.

My mom always told me I would grow into a man eventually, but that never happened, even during puberty my growth was minimal. By the time I finished high school I was a whopping 5'6" and weighed 110 pounds. This, along with my shoulder length blonde hair and extremely feminine facial features, had caused a lot of people to mistake me for a girl.

I discovered sissyfication on my eighteenth birthday. It immediately took a hold on me. I knew from gym class that I had a very small penis compared to most men. I was especially susceptible at this time now that I was technically an adult and would be forced to the live the rest of my life in this feminine body.

The changes came quick after that first day. I shaved my whole body (not that there was much hair to begin with), started crossdressing, and even began a workout regimen to make my body as female as possible. Within a few months, I had noticeably changed my body from that of a skinny boy to a young woman. While my chest was flat, my butt had become perfectly round and juicy, giving me a sexy curve from my petite waist. From the neck down, I was indiscernible from a woman. I had also amassed a respectable collection of items. A chastity cage, a realistic dildo, and I even had a few of my own outfits.

My parents were going to be out of town for the whole month and decided that, now that I was 18, I could benefit from having the responsibility of looking after the house myself. The timing could not have been better. I was getting bored of just fucking my silicone toy and decided I was ready for the real thing.

As soon as they walked out the door I grabbed my box of sissy things. I grabbed the chastity cage and locked it around my flaccid, two-inch penis, then laid out the schoolgirl outfit on the bed. I ran through the house naked, straight to my parents' bedroom and into my mom's closet.

She was the type of woman to never wear anything twice. I had hundreds of options of any type of dress or skirt or lingerie. I snatched my favorite garter belt and matching stockings. Wrapping the garter belt around my waist before sliding the stockings up my hairless legs, reveling in how slutty they made me feel.

After attaching the garters I sat down at my mother's vanity and applied my make up. I was going for a pornstar look and surprised my self with how excellent I did. Dark eye shadow and a cherry red lipstick made me the perfect whore, but I was more impressed with my exquisite application of foundation and blush.

I searched through hundreds of pair of shoes and found a perfect pair, strappy, bright red 6-inch heels. I made my way slowly back to my room, making sure to put one foot directly in front of the other and giving the imaginary man behind me a great look at my pantyless ass.

I pulled on the plaid schoolgirl skirt that matched my shoes and only covered half of my toned ass. Then tied the white top around my flat chest. I felt flawless. I admired myself in the mirror for almost an hour. I tried different ways to wear my hair and settled on pigtails. I tried different poses to see what accentuated my assets best. I even practiced my sex faces, perfecting my innocent look and my "ready for a facial" look. Happy with my progress, I pulled out an eight inch jet-black dildo and spent the rest of the night bouncing up and down on it as I watched my favorite sissy hypnosis videos.

I woke up groggy and confused. My headphones had fallen off at some point during the night but a sissy hypnosis video still flashed on the screen of my phone. The dildo had slipped out but was still shiny with lube and there was a wet spot on my sheets where my caged penis had been leaking. I felt hopelessly horny and knew that I couldn't wait any longer to lose my sissy virginity.

Soaking in the bath, I ran a razor over every inch of my hairless body. Triple-checking that I had not missing a single hair. Only stepping out once immaculately clean, inside and out. I looked down at my unlocked cocklet and smiled to myself. I felt at ease as the pink cage slipped back on. While my genitals felt restricted, a sense of freedom had washed over the rest of my body.

I sat at my mother's vanity again. This time wanting a more innocent look. I worked meticulously, every detail had to be perfect.

About an hour later I was finished. I felt my clitty stir in its cage and a deep twinge in my asshole as I finally allowed myself to take in what I had created. I was angelic. I had definitely gotten the innocent look, but something in my face still screamed, "I need cock."

After triple checking every aspect of my makeup, from mascara to nail polish, I headed back to my room and put on a black g-sting. I grabbed my phone and started taking pictures. After a thirty-minute photoshoot I decided on three pictures. For the first, I was on my knees, showing off my feminine thighs and small waist. The next was a close up of my ass; my asshole peeked around the string running through the toned cheeks I had worked so hard on. The final was my favorite, again on my knees, this time I focused on my top half. I laid my arm across my flat chest, covering my nipples. I put my pink lips at the top of the frame, careful not to show any distinguishing facial features.

I found a casual encounters website and started to create my ad. I wrote out the title, "Sissy (18) for BBC." I said that I was a virgin and needed to be "broken in" by a big black cock. I was too horny to worry that I might be asking for trouble by sounding so desperate. After attaching my photos, I took a deep breath and posted it.

I waited an hour before checking for responses. My photos seemed to be a hit and I got many responses from many large black men. One candidate stood out. Big_Daddy83. All he said in his message was that he was 6'4" and hung. His pictures confirmed this. He had a perfectly toned body and his cock hung just over halfway down his thigh. I messaged him immediately, telling him that I thought his cock was beautiful and would be honored to worship it.

After an anxious ten minutes, he replied. One word, "Address."

I typed out my address and held my finger over the send button. I felt myself get hot. Had I let this go too far? As my brain tried to scare me into backing out, I forced myself to press send. All the fear melted away. There was nothing I could do now. I started to worry, not about the fact that I had just invited a man over to take my virginity, but whether or not I would be able to please him. Do I look girly enough? What if he hurts me?

I didn't allow myself to get worked up. Instead I went to pick out what I was going to wear. As I walked in to my mother's closet, my eyes locked on an expensive looking wooden box. It contained her bridal lingerie, something I had never even considered touching. But somehow, looking at it now, it felt right, like I was supposed to wear it.

I opened it slowly, then took the white lace garter belt in my hands a carefully wrapped it around my body. Next were the stockings. After attaching them to the garter belt, I pulled up the white panties. The lace kept my penis snug in its cage and left most of my ass uncovered. I decided to leave the bra behind and finished the outfit with white, 6-inch stilettos. I spun around in front of the mirror. I couldn't have looked more perfect.

I debated just going as is but I decided to put on a skintight white, strapless dress to match the rest of the outfit. It came down to about mid-thigh and showed off my slim waist perfectly.

Just as I started to think about how much my guest was going to love it, I heard the doorbell and my heart leaped in my chest.

I ran as fast as my heels would allow me but before I could get to the door I decided on one last addition to my outfit. I hurried to my box of sissy things and grabbed a pink collar with black trim. In shiny gold lettering it said, "SISSY." It was the perfect contrast to my white angelic outfit.

I got to the door and took a deep breath before I opened it.

There he was. Almost a foot taller than me with the darkest skin I had ever seen. He wore a white tank top and gray sweatpants. His muscles bulged out of his shirt and there was an obvious bulge in his pants. He smug expression showed me that he was pleased with my appearance, but all he said was, "Turn around." Something in the way he said just made me want to obey. His voice was calm but powerful; it felt like he was radiating pure masculinity.

"Stop," he said as I had my back turned to him, "bend over."

I kept my legs straight as I pushed my chest to the ground, making sure to maintain a proper arch.

"Good girl."

I stood back up and turned to face him. He continued to examine my body for a few moments while I mustered up the courage to speak.

"Please come in," I squeaked.

"Thank you sissy. And refer to me as daddy from now on."

"Yes, Daddy," my clit twitched in its cage as the words left my mouth.

I walked him through the house and sat him on the couch before offering him a drink. He asked for whiskey and I tottered off to the kitchen to fetch it for him.

When I got back he was on his phone. Without looking up he told me to put the drink on the table and get on my knees in front of him. I responded with a, "Yes, Daddy," and did as I was told. As I waited, my eyes began to wander. But, every time I looked away he would snap his fingers, commanding my attention again.

I wondered what he was doing that was so important. I would look at his crotch, fascinated by the sizable bulge, then back to his face. He never looked at me once.

It felt like hours before he finished his drink. He savored the last sip before placing the empty glass on the table along with his phone. My heart fluttered when he finally looked at me.

"Have you ever done this before, sissy?"

I shook my head no and a slight smile escaped his mouth.

"Good," he paused, looking at me with a new found interest. "You will do exactly what I require of you or you will be punished. Is that clear?"

I nodded my head.

"Is that clear?" he repeated, slightly raising his voice.

"Yes, Daddy," I meekly replied. His forcefulness only amplified my desire.

"Now get up and take off your dress."

Again, I did as I was told. Turning around and shimmying out of the dress, making sure to display my girly ass.

He looked at me like a piece of art he was unsure the meaning of. His brow was slightly furrowed and he held his chin between his thumb and index finger. After a few more moments of studying me, he pointed to the ground at his feet. I took a step closer to him and returned to my knees. Next, he instructed me to remove his pants.

"You may look at it but do not touch."

It hung very low, past the seat of the couch. It was as thick as my wrist and as long as my forearm. If I had to guess it was about 9 inches and not even hard yet. Hiding behind his massive member were testicles larger than I had seen on any pornstar. I would be surprised if I could hold both in my hands at the same time.

After admiring his cock for what must have been a full minute. I placed a hand on top of each of his thighs and looked up at him. I must have looked desperate because he chuckled to himself before saying, "Ask nicely sissy."

"Please may I taste your cock, daddy?" I had forgotten about the rest of the world. All I knew was that I had to taste him.

He made me suffer a few more seconds before simply nodding his head. I lowered myself toward the ground to pick up the head of his cock with my mouth. But, in the moment before I wrapped my lips around that gargantuan tip, we locked eyes and something clicked inside of me. I took Daddy's shaft in my hand and lifted it up. I felt the sexual energy rushing through it as his heavy balls were fully revealed to me. I looked up at daddy again and gave the sluttiest smile I could before slowly taking one of his massive, cum-filled testes in my mouth.

The taste was overwhelming. It was pure manhood dancing on my tongue. His musk filled my nose as I allowed his ever-hardening phallus to rest along my nose. I licked and sucked back and forth between each ball, maintaining eye contact as best I could.

His cock had still not reaching its full potential when I started to make my way toward the tip. Running my tongue over and planting kisses on every inch of the underside of it. There was a jewel of precum leaking out of the tip. I took the base in my hand and gave it a gentle kiss, letting the cock juice stretch out from his cock to my lips. "Sissy is a dirty little whore, isn't she?" I bit my bottom lip and nodded my head while I picked up the rest of the delicious liquid with my finger and sucked it clean.

I moved to take the head in my mouth now. This would be the real test for me. He had gotten significantly thicker and longer by now. I had to open my mouth as wide as possible just to get the head in. I had given my dildo many blowjobs before but this was a whole new experience. The musk of his sex overwhelmed my senses as I forced myself to inch deeper and deeper, all the while making certain I did not use my teeth.

I started to struggle when I was just a third of the way down his shaft. I looked up at Daddy apologetically, my eyes watering with his rock hard cock pressed against my throat. He put his hand on my head and pushed down. I felt it bulge against the collar around my neck. Daddy kept pushing and I knew I was to going too have to make myself take the whole thing.

I fought my gag reflex as his monster continued to feed into my mouth. Tears were rolling down my cheeks now, mascara staining my face.

I must have lost consciousness for a moment because just when I thought I couldn't take anymore, Daddy was slamming my face into his crotch, fucking my throat. I could only get a small amount of oxygen with each thrust and just as I was losing consciousness again, he slammed into me balls deep and slowly pulled me off.

Multiple thick strands of saliva still connected his cock to my mouth. I heard him say something but I was shell-shocked by the throat fucking I had just taken. I was only brought back to reality when he grabbed the hair on the top of my head and pulled it to make me look at him. "I said, what do you say sissy?"

"Thank you, Daddy."

"Good girl. Now, show me your bedroom."

I had still not fully recovered and almost fell over trying to stand up, much to Daddy's amusement. I took his penis in my hand and began to walk to my room.

His erection was still raging by the time we got there. I turned around to face Daddy and slowly stroked him as I awaited further instructions.

"Get your lube and present your ass to me on the bed."

Again, I did exactly as I was told. I put my knees on the bed then leaned forward on my elbows. Just being in this position got me so horny I started to leak.

Daddy moved toward me and stopped when he got to the edge of the bed. He waited a few seconds before putting both hands in the waistband of my panties. He pulled them down and over my heels, then opened the bottle of lube.

"Are you ready sissy?"

"Yes, Daddy."

Daddy poured the lube directly on my asshole and massaged it in. He applied some to himself before lining it up with my virgin hole. The touch of his warm monster sent electricity from my hole through the rest of my body. He teased me with it, rubbing it in a circle around my sensitive ass. I held my breath when I felt him start to push it in. I savored the brief moment of building pressure before his head popped in. The pain was intense, but the deeper he went, the more pleasure I began to feel.

His cock seemed to go on forever, but by the time his heavy balls were resting on my taint, all the pain had subsided. As his cock throbbed, there was an overwhelming feeling of fullness and a powerful pressure on my prostate.

Daddy gave me time to adjust before slowly pulling his big black cock back out of my ass. I let out a long, slow moan as his meat retracted until there were just a few inches left inside me.

"Say it sissy," he growled at me.

Without even thinking, I begged for it, "Please fuck me Da-"

Before I could finish my sentence he shoved his cock balls deep inside my virgin ass. I tried to scream but nothing came out except a whisper. He continued his attack on my insides. With every stroke he would pause for a second, fully implanted inside me, then pull out and slam back in.

I never knew that I could feel like this. Despite his vigorous fucking, all I felt was pleasure. Not just in my ass but spreading through my whole body. I made all types of sounds I had never heard from myself before, all involuntary. Daddy's cock was turning me into a bigger slut with every stroke.

There was a pressure building in my lower abdomen. I had felt it before with my dildo but it had never been this intense, and it kept growing. It soon became very uncomfortable and I tried to tell Daddy to stop but my voice would not work, almost like the king-size tool in my rear was hypnotizing me.

I felt like I was going to explode, and then I did. The orgasm rocked my whole body. My eyes rolled to the back of my head, my ass convulsed around Daddy, my legs shook uncontrollably.

Daddy did not stop thrusting into me and my neither did my orgasm. It must have been thirty seconds of pure, full body pleasure. He finally pulled out, allowing me to recover.

"Are you gonna clean that up sissy?"

There was a sizable puddle on the sheets below where my locked penis had been. A string of cum still hung out of the pink cage. I turned around to face Daddy and pushed my face into the puddle, licking up all I could. I never loved the taste of my own cum, but putting on a show for Daddy made it extremely enjoyable.

I looked up at him when I had finished. He seemed pleased but I knew I still had a lot of work to do.

He lay down on the bed and effortlessly picked me up, placing me on his cock facing him. We locked eyes as I reached a hand behind me to line up his member with my hole once again. I bounced on his cock slowly as my hands explored his dark, muscular chest. He had fucked me as a sissy and now was making love to me as a woman.

I made sure to press my cheeks against his pelvis with every stroke. He began to let out his own low groans to match my feminine squeals and moans. The lust in his eyes told me he was getting close.

He picked me up off his cock and threw me to the side of the bed. Standing up he motioned for me to come to him. I crawled over on my hands and knees, making every movement as inciting as possible.

I reached Daddy and ran my tongue from the bottom of his low-hanging sack to the tip of his head, getting a taste of precum. Then, using both hands on his shaft, I began sucking and slurping. I made it sloppy, trying to coax every drop of cum from those delicious balls.

He pulled out and started stoking rapidly. I looked him in the eyes with my head tilting back and mouth tongue stuck out, silently begging for his cum.

I knew it would be a big load but the volume of spunk still amazed me. The first shot covered me with a thick rope from my forehead to my chin, stretching across my left eye. Three more ropes of the same size covered my face and filled my mouth before his orgasm started to subside. By the time he finished, I could only open one eye and his thick semen was overflowing from my mouth.

"Don't you move sissy," he said, his voice more relaxed now.

There was a flash before he told me to swallow. I almost didn't want to. His cum tasted completely different from mine. While mine was watery and salty, his was thick and sweet. It was like a delicious, warm smoothie.