My Sissy Fantasies Coming True

I am not sure why I am the way I am but, not having a father figure and growing up in a house with three women could have something to do with it. I am addicted to women's clothes, I love the look, the feel, and I love dressing up. We lived not too far from a truck stop near the interstate, and I would frequent their magazine rack. There was 20 feet of nearly every type of perversion known to man on that rack and several that were based on crossdressing, some gay some not, a lot included spanking. Pictures galore along with stories, ah the stories, a lot based on "Daddy" finding out his son was a sissy. Spanking punishments followed, all with the son in his sissy clothes. Some punishments went past just spanking with threats like; "So, you want to know what it feels like to be a woman do you?" Some very descriptive stories, a lot of pictures depicting some very vulgar, humiliating acts.   Acts that I was wishing would happen to me. I never once purchased a magazine, but I stole hundreds over time, kept them locked in the barn away from the prying eyes of my Mom and sisters. I stole panties too and bras from our laundry, I also swiped the some from neighbors, cousins and Aunts when I got the chance. Those were also hidden in the barn for my pleasure when I was able to spend time alone.  

That time alone, I would fantasize about being taken to the barn or woodshed by my father. He would be so pissed off, so ashamed of his son. Sometimes I would position myself in my sissy things, bent over a hay bale, legs spread, bottom arched, waiting for that Razor strop to strike. I imagined Daddy telling me how ashamed he was with each strike, how ashamed I should be. I was so into my fantasy that my body would recoil from the imagined strike. Sometimes I would hold off from peeing until I was bent over taking my beating, I would piss myself as if the pain Daddy was inflicting made me lose control. I could make myself cry from the vision I was seeing in my mind. When I got down to the other punishments, the ones when Daddy would say; "You want to know how it feels to be a woman! I'm going to show you how it feels!" I would imagine I was forced to my knees, and I would roughly push a pickle or a cucumber past my lips, pushing it as far as I could take it. Or I would bend over spread my legs and force it up my sissy pussy. Sissy pussy, I was sure that would be a term my Daddy would use. As I did one of these acts, I would rub myself through the panties until I came. Then would come the rest of the humiliation from Daddy, I would be made to lick those panties clean. After it was over, I would lovingly hand wash my sissy things making them ready for the next time I could be punished.

When I left for collage, those treasures went with me. I found a two-bedroom house that I could afford it was on the edge of town. Some boy's grandma passed and left it to him. He was miles away in the city and was looking for a little income from renting it, I just happened along at the right time.  

The first month at school was hectic, but time spent at home was time I spent in sissy clothes.   I got a part-time job at of all places, a porn shop. It actually paid better than anything else I could find. People would bring in used magazines and traded their magazines 2 for 1. I had the opportunity to browse the magazines before they were slipped into the plastic covers; some got slipped into my backpack.   Magazines weren't the only things that slipped into my backpack. Sexy panties, nighties, and an occasional toy. Other than me stealing from the store, I was a model employee I worked hard, always showed up for work which was more than could be said for most of the other employees. That was probably why when John, the owner, called me to his office after closing one night, things went the way they did.

"Robert," He had said. "Take a seat."

I sat on the same side as him in a chair he had pulled up. He proceeded to hit buttons on the computer. I watch as the screen showed each and every thing I had stolen, videos taken from the security cameras. Each scene was captured by at least three cameras. Showing different angles of me stealing John's shit. When he was done, my eyes were red, I was exposed not only for being a thief but for being a sissy.

"I hope you know that for the amount you have stolen it is a felony, that means jail time." John said. I broke down in tears, so scared, so ashamed. "I can call the cops right now and your life as you know it is gone. The people at your school will know, not to mention your family. You do have family?"

"Yes." I said, wiping my nose and face with my sleeve. "I am sorry, I will pay you back." I begged.

He looked at me long and hard then said; "Your Daddy ever spank you?"

I took in a deep so fast breath that it almost had me choking. When I regained what little composer I had, I answered him. "No, I, I never knew my father, he ran out before I was born. My mother never remarried, I lived with my mom and two older sisters."

"Well that explains a lot of things." He looked me up and down before adding. "I can cut you a break, not call the cops, but it is going to cost you." He waited for my reply.

"Cost me? What do you mean?' My voice quivered.

"You will strip right now, bend over, I am going to blister your ass with my Razor Strop, for starters." He opened a drwaer and pulled out what looked like a well-used leather strap and laid it on the desk. It had a handle and a length of leather with a matching length of something under it.    "Barbers use these to sharpen their straight razors, Daddys use them to show sissy boys like you the error of their ways. Which will it be, call the cops or?" His fingers tapped the leather.

I gulped and stood on shaky legs. "Right here?" I asked looking at the cramped office.  

His eyes met mine; he rose, pulling me up by the neck and grabbed the strop with his other hand. We went through a doorway behind his desk. On the other side was a room filled with furniture designed to restrain someone during, well during whatever the other person did whatever he wanted to do. "Strip!" I stated with my shirt, I was so embarrassed because under it I had a thin sports bra that held almost nothing but was frilly and pretty. His hand went to pinch the nipple that was hard and pushing against the fabric. "You can keep this on." I kicked off my shoes and unbuckled my belt, sliding the pants down revealed a matching pair of panties. He snorted. As the pants slid further down it my thigh high stockings came into view, his hand slid across the front of my panties. They were wet and I knew it, but the bulge was barely visible.

"I have to pee." I said in a shaky voice. He led me to a corner, a toilet sat there in the open, no walls. There were restraints on the floor in front of it. I started to lower my panties in front to pee.  

"Sit and pee like the little sissy cunt you are!" John demanded.

As I turned and lowered my panties and sat. "That's the tiniest little wee wee I have ever seen. Spread your legs and let Daddy see that." When I did, he let his hand slide down aiming it into the bowl. When I had finished, he pulled me off the toilet by my hair and forced me to my knees.   "Crawl." Was all he said as he tugged on my long hair. He guided me to what looked like A bench that had a saddle on it.

"Bend over that saddle, stretch your arms back. When I bent over my toes barely touched the floor. He attached leather cuff to my wrists. A belt came over my back, cinching my waist and causing my ass to round up and back lewdly. I was breathing hard and fast, my fantasy coming true, but I was scared as hell.   I couldn't see him as he walked behind me, but I could feel his eyes on me, I could feel him looking at my panties still lowered from using the toilet.

"That has to be the smallest bag of balls ever! At least your fat sissy ass makes up for them." And the strop hit.

It sounded like a gun shot, the scream I heard echo in the room was mine. "Tell Daddy you are sorry you are such a sissy." The strop fell again.

I screamed out; "I'm sorry I am such a sissy Daddy!"

"Tell Daddy how ashamed you are to have him looking at your bare cunt as he spanks you."  The strop exploded again. Between every demand from Daddy the strop worked it's way down my ass covering it thigh to thigh.

I was bawling. "Daddy I am so ashamed, so ashamed your looking at my bare cunt. Please stop Daddy!"

"You should have said you are so sorry Daddy has to look at your bare cunt, So sorry Daddy has to see his little sissy boy's naked filthy cunt!" Daddy drove the strop home at the end of each sentence.

I screamed, breathing hard, and snot running from my nose as I bawled. "Daddy I am so ashamed, so sorry you have to see your worthless sissy son like this, so ashamed you have to look at my sissy cunt!"

"I know you can't be my son, you sniveling little shit! A tiny dick no bigger than my little finger and a bag of balls that barely big enough to hold a grain of rice. When I am done with you, I am going to blister your mom's ass with this strop for cheating on me!" He gave me five in fast, rapid-fire order. He laid the strop on my back.

When he stepped in front of me, he was naked. His cock long, thick and hard, the head was smaller than the thick shaft, it looked like a torpedo. I turned my face away. I knew I was eventually I was going to suck it, but I was needing more pain. I wanted to remember this spanking for days to come. "No Daddy, I won't! I won't you can't make me do that!"

He realized what, I needed. He grabbed that Razor Strop from my back and laid it to my ass. "You fucking little faggot! You are going to beg Daddy for this cock!" The strop hit twice for every sentence Daddy uttered, fast and hard. "You hear me you little panty wearing, cock sucking, sissy little faggot! You are going to suck your Daddy's cock and swallow all of Daddy's cum you hear me!"

After several hard fast swats I surrendered. "Yes Daddy! Yes I want to suck your big fat cock Daddy. Please Daddy! Please let me suck you let me swallow your cum Daddy!" I felt the bonds being unfasten and I laid there over the saddle catching my breath. When I was able I slumped to the floor, I could see Daddy setting on the edge of a chair, his balls hanging down his cock standing straight up.  

"Crawl!" Was all he said, which was good because I didn't feel like I could walk. I crawled between his legs and had my first taste of a man's balls. I licked and sucked softly letting his cock rub against my face. I didn't get to spend as much time there as I wanted, he pulled me up by the hair making me kneel between his legs. He laid his cock under mine. It looked so pathetic. "Jack off on my cock." My little dick was hard and dripping, it didn't take long for me to lose control and erupt, covering Daddy's cock. "Now suck me clean!"

I had tasted my own cum many, many times but never as a condiment on a hard cock like Daddy's. I was glad I had practiced so often on cucumbers, I was able to take most of Daddy's cock. I must have been doing it right because Daddy erupted fast and it was all I could do to swallow it all. He was breathing hard and holding my hair keeping my face tight against his cock.

As his breathing eased, he said. "Now, you need to thank Daddy for your spanking and for him letting you suck his cock."

I was at a loss; I wasn't sure what he wanted but would soon find out. He stood, bent over, and said. "You may kiss Daddy's ass."

I buried my face between his hairy cheeks and thanked him very, very well. Letting my tongue work his butt hole over, kissing it ass I made love to him with my tongue.

After when we had redressed he said; "Tomorrow when you come to work you are going to be fully dressed as a woman, you will show up for work every day full make up everything. Do I make myself clear?"

"Yes Daddy." And so began the next phase of my life.

By 

Sizzlebuns