Groomed all her life to be a special girl, Dee is ready to be sexually awakened, a project her father will take care of according to her mother. He shows her how to please a man orally, but when his need to breed drives him away, Dee mother is willing to join in the training to have him finish teaching her.
Ever since I can remember, my mommy dressed me up like a girl and we did all the typical little girl things like having tea parties, collecting dolls, and shopping for frilly dresses, usually in pink since it’s my favorite color in the whole world. For a long time, I assumed other families did this with their special girls. I mean I never asked anyone after all why would I? I thought it was normal, I didn’t even realize I was different from other little girls until I played doctor with a neighborhood boy.
We moved shortly after that and I pushed the information to the back of my mind. I honestly never thought anything else about it until the day I came of age, the day everything changed. Mother said, she will have daddy teach me about sex. She called daddy to the kitchen and told him I was of age to be taught about the birds and the bees. Oh Daddy, I playfully patted his beefy arm. I know all about that. You do he asked? Sure, when a boy loves a girl they get married and then they have babies. But do you know how that happens he asked me? The romance novels mommy had allowed me to read never went into details on that part. There was just a lot of meaningful looks, hand holding, and passionate kisses. “More than anything, I wanted a boy to kiss me passionately”. Well mother asked, do you know about blow jobs, masturbating, and intercourse? No, I answered. Then daddy will start teaching you tomorrow.
I remember getting a new pink short dress with matching panties. I loved my cute pink dress, the shortness of it showed off my long legs and my matching panties. When I first started wearing it mommy told me to go show daddy how well it looked on me. I remember going into the room and he was reading the news paper. Standing in front of daddy I asked him how he liked my new out fit? When he looked at me I lifted my short hemline to show him my matching panties. Very cute daddy said, he continued to look as I twirled around in front of him. Mommy had been so proud of me being willing to wear cloths that she picked out for me.
The next day mommy said it was time for my father to teach me about sex. I know your father will do a good job with all of this, but you need to do as he says mommy told me. Despite his obvious embarrassment mommy told me he was determined to do his best for me. You’re going to do just fine daddy, I told him as I patted his arm. I didn’t want him to feel bad. You’ve always been there for me and I trust you to help me with this, I told him. Good, daddy smiled softening the tension from the lines around his mouth and eyes. Let’s go down to the basement he said. Now normally I didn’t go down there. Mommy would go down and spend time down there and sometimes daddy joined her. Daddy had spent untold weekends installing carpet and paneling and heavy wooden furniture. The basement had always been called daddy’s man cave. He retreated there when he got overwhelmed by femininity, his code for needing a break from all the girly things I did with mommy.
Still my lesson needed to be taught so I followed Daddy down the thirteen steps. Oh, you moved some furniture around since the last time I’d seen it. There was a big bench thing or what ever you call it in the middle with leather straps on it. That’s, well we’ll get to that. I couldn’t help staring at the strange rocking horse with a rubber thing rising up from the seat. The more I looked at it I realized it was a fake cock. I thought that was a weird thing to have where you sit. I started feeling weird deep inside my stomach. Not like I was going to get sick, but almost like I had to pee. Your mother like’s to ride that horse daddy said. I will conditioned or I mean educate you on that in time. You know about why mom like’s to ride it he said.
When do we start, I was now excited to see what daddy had to teach me. I could tell he was still nervous so I walked up to him and put my arms around his neck. Then I gave him a big kiss on his lips. I continued kissing and my embracement until he responded by putting his arms around me and gently squeezed my ass as he kissed me back. When we broke our embrace I smiled and asked daddy what do you want to show me I asked? Well a man is going to want you to play with his cock and suck it. Do you think you could do that? Yes daddy, I can do that. He removed his pants and underwear standing in just a T-shirt he told me to touch his cock. I reached out and cupped his big heavy balls. Then lifted his heavy cock as it started to grow. I was watching it become erect, I was surprised how big his cock became. Standing straight up now the big cock head was purple and bobbing as it throbbed. Go on now and suck on it he told me. I opened my mouth and put the head of his cock in my mouth. I licked it with my tung, it was so soft.
Daddy told me he wanted me to go up and down on it and try to get it down my throat. He held the back of my head and he moved his cock back and forth. That’s it he said, good job keep up the sucking he said as he stood over me. I sucked his cock the best I could. Then after several minutes he told me to stop. Removing his cock he told me to masturbate his cock. Doing just like he showed me his cock exploded all over. Wow, so much cum, came from daddy’s cock I was impressed. I let go once it stopped ejaculating and stared at it as it continued bobbed ever so slightly. Now baby I want you to lick the tip of my cock which I did. You will need to get used to the taste of a mans cum he said. You will need to swallow it as it fills your mouth. Oh daddy, I don’t think I will like that. He told me I will get use to it and even like the taste in time. From now on I will have you eat some each time we have lessons so you become use to it he told me.
Then he said, by the end of the month I will be able to take his load in my mouth and swallow it. By the end of the month I asked? Yes, we will practice every night until you can swallow my load. He told me to play with his cock and as I did I noticed my little cock was stiff. I told daddy my pee-pee was stiff and I asked him if I needed to play with mine? He told me to remove my cloths, so I did as he said. My pee-pee standing stiff was very small compared to Daddy’s. His was a massive eight inches or more and mine was hardly an inch or two at best. When daddy looked at it he smiled and told me to sit on the table and lay back with my legs hanging off the edge. Now my pee-pee stood straight up and was really hard. Daddy lowered his mouth to it and sucked on it. The warmth of his mouth felt so good and after thirty seconds I leaked some cummies “as mommy called it” into his mouth. When he finished sucking and licking my hairless sex organ, he stood up and told me he will need to put me in chastity? A young girl like you needs to keep her parts contained. I didn’t know what he was talking about, but then I was still trying to recover from the sucking he gave me.
The next day daddy took me to the basement again and had me remove all my clothes. My white pail hairless skin looking milky white except for my pink nipples and pink cock head. Daddy sat in a chair and told me to stand in front of him. He took some plastic tub and fitted it on my small cock and locked it with a tinny padlock. The tube felt funny and I asked what it was for? He told me so I would not get sexually aroused during training. He told me to get on my knees and play with his now exposed cock as he laid back and watched me. When it started to grow he told me to kiss it and suck on it but keep jacking it at the same time. Daddy’s cock grew very fast and once hard I sucked and licked and played with it for a long time. Daddy liked it because he kept grunting which I found funny. He kept saying I was a good girl.
He told me he was going to cum and wanted me to catch it in my hand, so I did as he asked and when it started to run out of my hand he told me to lick some up. I tried it but it was warm and slimy and tasted kind of salty. I made a funny face after my first taste and daddy told me to keep licking at it until it was gone. He watched me and kept telling me that I was such a good girl each time I swallowed some. Encouraging me to keep licking it out of my hand. Then he told me I was such a big girl when I finished it. I told daddy my cock was trying to get stiff but the plastic tub was holding it down. He told me that is what is supposed to happen.
He continued saying, Dee, you’re a sissy and sissies only get to squirt when they are being penetrated. Do you want to squirt he asked? Yes daddy my cock wants to squirt I told him. He asked me to bend over and he rubbed something slippery on my butt hole. I felt him stick a finger in me and asked how it felt. I told him it hurt and he said relax and the hurting will stop. After a minute or so he started moving it in and out which started to feel good. My pee-pee was harder now than before as it strained to get free. Soon he put another finger in side me and kept the motion going. before I knew it I was pushing back on his hand. Good Dee he said, keep humping my fingers. It feels good don’t it he asked? Yes daddy, it feels real good I told him. When we finished he told me tomorrow we will try a dildo and then a plug. I was eager to continue out sex lesions because daddy made me feel so good.
The next session daddy used a small dildo on me and I leaked just a little bit. When I was loosened up from the dildoe he fitted a plug in my ass which made me feel full. Now Dee he said, you’re doing so well I want you to give me a complete blow job and swallow all my cum. Now it will fill your mouth full but you need to swallow it as fast as you can, understand? Yes daddy, I will do my best but you have such a big load daddy. I know honey but you mother could do it and I know you want to make her happy don’t you? Yes daddy, and I want you to be proud of me also. Okay he said, then take my cock in your mouth and sick it. This took what seemed forever but I finally felt it growing and daddy said swallow fast, as he shot the first streams of cum followed by a gush of cum. I gulped several times but there was so much it leaked out of my mouth and dripped off my chin. I could not keep up with the massive amount and pulled away. The last two streams went in my face as he finished. Good girl he told me but next time you keep your mouth on my cock until I finish. Okay daddy, I am sorry I couldn’t eat it all fast enough.
Daddy told me to keep the plug in my rear so I get what he called “Conditioned”. I asked what was I conditioning for? Some day you will meet a nice man who will be interested in you and he will want to have sex with you. He will want to put his cock in your ass and have sex with you. You need your ass stretched so you can accommodate his cock. I asked how big will I need it stretched? He told me when I can take a dildo and it don’t hurt much, then I will be ready.
I asked daddy why my pee-pee was so small? He told me there are men and then there are boys who grow up to become men. Just like their are women and girls that grow up to become women. You Dee are what we refer to as a girly-boy or better known as a sissy. Sissies he told me, are boys that should have been a girl and that is why your mother raised you as a girl. You will hopefully meet a nice man and marry him some day. I told daddy I would really like that. He smiled and we continued my training.
About a month and a half passed before I was able to eat daddy’s load of cum. I also had mommy show me how to ride the rocking horse with the dildo. Mommy showed me how it went into her pussy and she would rock back and forth. She would keep rocking until she started to shake and saying O-my, O-my, until she had what she called an orgasm. Then she would sit still until she was ready to get off the rocking horse. She would wipe all the water off since it became wet from her. I think she must have wet herself while riding it. Then it was my turn to rid it but the dildo went in my ass since that was my only hole. Mommy told me men will want to mount my ass when I date them. I asked why and she said that is what boys do when you find one you really care about.
Mommy told me after I have ridden the rocking horse for a month or more, daddy would show you how a boy will mount you. When that day came daddy strapped me down on the table with my ass in the air. I asked why I had to be strapped down. Mommy told me so I would not try to get away. I still didn’t understand what she meant. She watched as Daddy smeared lube on my hole then he lubed his cock. That is when mommy told him to go slow and I knew what he was going to do. I asked mommy, is daddy going to mount me? Yes sweetie she said, just relax and he will enter you. Just then I felt pressure being applied to my rear hole and something slipped in. His cock slowly slid in as I felt my ass stretch wider than it ever had before. I told mommy it was hurting and to tell daddy to stop, but she told me to relax and take his whole shaft.
I started to cry as he kept pushing it in farther and farther until it felt like it was inside my belly. Their daddy said I am all the way in and he stopped pushing as I adjusted to his big cock. We stayed that way for a minutes or two then he pulled out some and pushed back in. He did this slowly for a while then picked up the rhythm. He kept on for some time in which I started to enjoy the feeling. I started moaning and mommy said, that’s it honey just enjoy daddy riding you. It feels good doesn’t it he asked? Yes, oh, oh yes, I answered,. Then I felt myself squirt at the same time daddy climaxed inside me. I felt his big cock pumping cum in me time and time again until daddy stopped moving. Mommy told me I did real well and daddy will be making you squirt many more times.
While I laid there strapped down catching my breath daddy pulled his cock out and mommy plugged my ass with a large plug right away. I yelled as she forced it in me. Then she asked daddy, how was she tight? Yes daddy said, she will stretch out after several more fucking’s. Mommy told him to make sure he plugs me after each time he fuck me to ensure I stretch properly. Then mommy came and unfastened the straps. Oh I squealed as I tried to get up. Mommy asked what was wrong and I told her my ass was so full I could hardly stand straight. I was told I had to keep the plug in for and hour. She told me I should lay down and rest while the dildo loosens me up some. When it was removed it hurt but then a lot of daddy’s cum ran out of me when I stood up. Mommy old me to go take a shower which I did. I had a hard time walking after daddy mounted me.
My training went on for several more months. Riding the dildo rocking horse and sucking daddy’s cock and swallowing all his cum. My pee-pee was locked up all the time but I would squirt when riding the horse and when daddy fucked me. I didn’t need to be strapped down any more I would sit on daddy’s cock as he sat in a chair. I would ride it like the rocking horse until I squirted which didn’t take long. Daddy would make me stay seated on his cock until he climaxed in me. When I bent over daddy could slide his cock right in me and it barely hurt at all. Daddy told mommy I was ready to date which made me happy.
“SM” Sissy Maker