A Sissy Story

[tuppinsinmo]

Talk about a sissy I guess you could say I am one. I think it started way back in grade school. Our school was small in fact our town was small, only a population of 450. In my fifth grade class there was only ten of us, and I was the smallest boy in class. There was a girl named Mitt, she was big I mean she was pretty plump and that meant she already had tits to a degree. At ten years old I was interested in seeing girls naked, I wanted too it was all I ever thought about. I was such a coward I would look up under the school desks and try to look up the dresses. My reward was to see those cotton panties when they would suck up in the girls crack and I could see the whole out line of that pussy. And if I got really lucky the panties would suck up one side in the crack, oh man. I used to pray let there be a hole in the panties.
Mitt sit behind me and I would look at those tits, people were poor in our town and at that age none of the girls wore bras so you could some times see the little nipples press through the cloth.
On this day I dropped my pencil, I got out of my chair and got on my knees to pick it up and of course while on the floor examined all the girls around me to see what I could see. I couldn’t believe my eye’s Mitt had no panties on, I know my mouth dropped open because I thought my young heart was going to stop. There was the smooth skin and a deep crack between her legs, and right toward the bottom of the crack a bit of a opening and I could see something I later learned was labia lips.
I couldn’t help my self, I stared, I wanted to touch her, I had to touch that wonderful sight, I think she knew I was looking, because she pulled her legs wide apart and scooted down in her chair.
I don’t know what made me do it, I couldn’t control myself, she was so close I reached out and put my finger in that little opening. She didn’t move, she didn’t yell, she only scooted down further in the seat pushing my finger in that hole.
It was so hot, it was so silky and so wet, I forgot I was in class, I forgot about everything, my dream was being answered, God loved me and heard my prayer, I pushed my finger in deeper. I could feel the little bumps on the top of that hole, I could feel the tight skin wrap around my finger, I felt the wetness of it and wondered. I felt my own hairless cock grow hard, really hard for the first time in my life, I felt something else as I pulled my finger back and pushed it in again, she moved a little, and I think I heard a moan and my little cock jumped in my pants and some kind of stuff came out the end of it in my pants. Just then Mrs. Pits grabbed the back of my shirt, I felt my self being pulled to my feet, she was saying what do you think your doing Rickey, are you looking up Mitt’s dress. I stammered no I wouldn’t do that. My finger had slide out but it was all wet, Mrs. Pits was pulling me to the front of the class. She was saying something to me, I don’t know what I put my finger in my mouth and tasted a taste that can’t be explained in words, the smell was musky and good and yet wasn’t good but I fell in love with that taste.
Everyone was laughing at me, I looked down and realized I had a big wet spot showing through my light brown pants, someone said Rickey pissed his pants. I knew it wasn’t piss because it smelled funny.
Mrs. Pitt’s made me bend over the desk and she got her wooden paddle and I felt it come down on my ass, damn it hurt. My cock pressed in to the desk top, and it was still hard. I couldn’t believe it, she grabbed the waist and pulled down my pants, my bare ass was pointing out for the whole class to see, she hit my bare ass with that board four more times.

 

[tuppinsinmo]

part 2

In this class I will not have little pervert boys looking up girls dress’s she was saying. And when she stopped hitting me, I stood bent over the desk my bare ass showing, tears running down my cheeks. I turned around forgetting the room had all the other nine class mates my little cock dangling out in front of me as I pulled up my pants. She said go to the bath room and clean up, you nasty boy. Everyone was laughing, some of the girls were pointing at my limp little cock. I wanted to run away and never come back. I went to the bathroom, and washed my pants, the juice was clumpy, I licked my finger, clean, then took paper towels and dried my pants. When I got back to class, Mrs. Pitt’s had pulled my desk up next to hers and it was facing the class. I sit down everyone was staring at me. At first I thought I was going to die, but then something happened. I looked at Mitt’s for the first time. She wasn’t laughing but smiling, I looked down under her desk she pulled her legs wide open even placing one leg on the outside of chair so that her whole pussy was visible.
I have no ideal what was said in the rest of the classes that day. Every time I looked back Mitt’s would have her legs open or would open them. I know my little cock was hard again and a good thing my pants were already wet because that juice came out again.
Over the next few days nothing happened, Mitt’s never said a word, and I was to scared to drop my pencil so class went on. The teasing stopped, in fact some of the other boys asked me if I had seen anything, and I said no.
Sat came along and as I had finished all my chores, I decided to go horse back ridding, I wasn’t sure why I did it, but I headed for Mitt’s farm. When I rode up, her older brother saw me; he didn’t know anything about what happened in class because he was in high school. He demanded what did I want and I said to see Mitts. She came out and I asked if she wanted to go riding with me. She asked her dad and he let her, she got on the saddle behind me and off we went.
Mitt asked me if I had enjoyed putting my finger up her private, I said yes, it was worth the whipping. She put her hand on my cock, unzipped my pants and pulled it out. We were riding on a old trail through the woods, so no one could see. My little cock was hard soon as her hand touched it.
You know it is only fair I get to feel your thing being you felt of me. We stopped and got off, I said can I feel you again, she pulled up her dress, and I started running my finger in that crack and she was rubbing my cock up and down. She took her dress off and I saw those tits, not really all that big I guess but they seemed large to me. She ordered me to suck the nipples. I did so with out pause, then she ordered me to quit fingering her but to lay down with my head on one leg so I could lick her pussy she put the other leg over my neck and as I licked her pussy her juice really came out and she held my cock, I felt that juice come out again. I glanced up as she licked it off her hand then went back to playing with my cock. She began to work up and down on my mouth, pulling my face in to her pussy with that leg over my neck till I almost couldn’t breath. The her whole body jerked and her juice was thicker and tasted different. When she let go of me and lay back my face was wet with her juice.
Over the next few months every Sat I would go to her house, soon she had me in the barn and was ordering me to put my little thing in her hole. My first fuck was wonderful, I will never forget how wet, how tight, how sweet it felt to lay on top of her, my hands clutching her little tits my cock going in her and how fast my juice dumped inside her.

 

[tuppinsinmo]

part 3

After that Mitts would find ways to make me fuck her, I mean like at school on recess she made me go in the janitor’s closet and fuck her when I was so scared. I wanted to stop, Mary was starting to pay me attention and Mary was so pretty but Mitts said if I quit being her boy friend she would tell Mary how bad I was and how I had this little bitty cock and how I had made her do bad things.
As time went on summer break came, Mitts was starting to get hair around her pussy, and she ordered me around like a dog, she even decided one sat that we would spend the whole day together and every time she had to pee she was going to make me drink her pee. We would stop riding in the woods, she would make me get off the horse lay on the ground and squat over my face she would push her pussy right down on my mouth and piss. I didn’t really like the taste but she insisted that I drink it all and if I let some of it get on my face she would squeeze my balls till it hurt so bad. Once she sit on a log and took a shit, and she ordered me to lick that shit out of her ass because she was not going to use leaves. I cried as I licked that stuff, it stank and it didn’t taste good, and I wanted to get away from her.
Yet something pulled me to her, I guess I didn’t like some of the things she made me do but I liked the sex. We would stop at the creek and she would make me wash her, and brush her hair, and when she wanted fucked she would make me do it. Then she started having a time where she would bleed. I was scared, I didn’t know what it was, but she said it was normal for girls her age. She would make me wash her bloody pussy. Then on the day she was almost done bleeding she made me fuck her, she was into it more then normal she really rode my cock.
One day her brother showed up at our farm and he told me to take a walk with him. He said he knew what I was doing to Mitt and if I didn’t do what he said he would tell his old man and his daddy would shoot me. I knew he was telling me the truth so when he pulled out his cock and told me to suck it, I did till his own thick white juice came in my mouth.
Now I had Mitt ordering me around making me do her chores, fucking, sucking, being her piss bucket when she wanted me too and if that wasn’t enough, now her brother was fucking my mouth two or three times a week. Then one day, he came out to the barn where I was doing some of Mitts chores while she was sitting watching me. He told Mitts he was going to use her bitch and she was going to watch. I didn’t want to, I wanted to fight but I was to scared, I wanted to run but I didn’t, He fucked my mouth, but then he stopped and pulled his big thick cock out of my mouth very hard. I realized it was sorta pretty, standing that with all that dark hair around it, then he told me to drop my pants, I did, my own cock was hard, he told bend over and hold on to the stall. Then he pushed my ass apart and drove his cock in my ass it hurt so bad I screamed, tears ran down my face, he fucked my ass hard, I looked and realized Mitts was laying on the hay her dress up, her fingers inside her cunt pumping away. The bitch was enjoying watching me get ass fucked, she liked seeing me cry. And all at once her brothers cum shot up my ass, I felt like I was going to shit, but yet it felt wonderful, hot, and slick.
Mitt had a huge orgasm and all at once my cock was shooting my juice out in a flood of cum like never before. Then her brother laughed and walked over, laid on top of Mitts and fucked her hard for a very long time till his cum was oozing out of her cunt. My own ass hurt but he made me lick his cum out of her pussy.

 

[tuppinsinmo]

part 4

Over the next few months this became a weekly thing, every day I would fuck Mitt and then once a week her brother would make me give him a blow job or he would fuck me and always Mitt would sit by and finger her cunt, sometimes he would fuck her too but not often.
After months of this, her parents went going out of town, so they told me to see if I could stay with them. My parents said yes, I didn’t want to in some ways but I guess by now I liked being there bitch. I would lie in bed at night and dream of fucking Mitt or sucking his cock or getting fucked and jack off.
When I got to there house, he met me at the door, he told me to strip off my clothes, I did so Mitts was sitting in a chair watching I thought he was going to fuck me, but instead he handed me one of Mitts old dresses and her dirty panties and told me to put them on. He had her put make up on my face. They told me I was nothing but a little bitch and needed to learn to look the part. From now on I would wear dresses when we all three were together.
It felt strange but it also felt good, I like the feel of the breeze coming up the dress on my legs and cock. I was made to cook, do house work, and even watch him fuck his sister on the couch and then lick them both clean and then wash them in tub. He made me get on my knees and dress him and undress him, even taking his shoes off and licking his stinking feet clean.
By the end of the first day I guess I was the perfect little bitch. That night he made me lay on my belly with my head between Mitts legs eating her pussy while he fucked my ass. Over the next few days I was getting used to being a woman I was not even allowed to stand and piss I had to squat and if they caught me standing he would whip me. Toward the end of the week I was shocked when they called me from doing dishes to find four of his class mates and two of ours in the living room. They all laughed at the little bitch, then he made me bend over the chair arm and ripped my panties off, look his little dick is getting hard, the four boys took turns fucking me, while my own classmates each took turns fucking Mitts then making me lick there cum out of her cunt and lick there cocks clean.
My cock had come so many times I had no cream left, and my ass was so sore it hurt to shit.
Over the next few days a different group came every day and I was the bitch for everyone. Mitts was like this wide open ***** fucking ever dick, and I was this ***** who either sucked the cocks. Cleaned the cum, or got ass fucked.
Over the next few years, I was nothing but the bitch, and I loved it, by now every boy had fucked me and every one had fucked Mitt too. I was now sixteen and I almost lived at there place, we were in the barn and I was in my newest dress Mitt and her brother had left me there and I was doing some chore bent over when Mitts dad came into the barn. At first he laughed at me, then he called me a queer, then he pulled out the biggest cock I had ever seen and I didn’t have to be told I was on that cock like a hungry dog, sucking and licking he filled my mouth with so much cum I barely could hold it all be fore I swallowed. Then he made me bend over and he fucked my ass, I know my ass was stretched already but was no way ready for that big ole cock. He fucked me and fucked me and fucked me, I didn’t hear when Mitts came in the barn or her brother, I didn’t see Mitts as she had stripped, now she had a great body and huge tits I didn’t know she was licking her dads balls as he fucked me ass. But I knew when he came and I cam with him.

 

[tuppinsinmo]

part 5

So life went on, now the only person that was not involved in this sex was her mom. I don’t know if she ever knew, because Mitts got pregnant and I was told to marry her which I did. I don’t know whose baby it was, could have been anyone’s in town or her own dad’s. I don’t think it was mine because I didn’t get to fuck her much any more. Even in the locker room the guys would take turns fucking my ass.
I finally put my foot down, with the baby, we needed to move, at first she said no but I won and we moved to a town in AK not to far from home but far enough to get a new start.
The trouble was I missed it. Two weeks after we were there, I told Mitts be the ***** that she is. And she would go to the bar and bring guys home. I now had a good job at the mill so I bought really sexy dress’s for me, and nice panties and niceties. I would let her dates sleep with us, and often in the middle of the night I would find some hard cock up my ass. I loved sucking those cocks after they fucked my wife. Word got around fast, and before long guys was coming over from other towns, and they were willing to pay to fuck Mitts or me. The money was good, so good I quit the mill. I had nice long hair and my legs looked great in panty hose, we would even go places now that the whole town knew I was a ***** and so was she dressed like a woman. I was never allowed to fuck any guy or other woman, Mitts always gave my cock plenty of used pussy.
One night a group of black guys came down to our town from Little Rock, things were going great, they each fucked Mitts two had fucked my ass, then the trouble started, they started getting ***** and wanted Mitts to go back to Little Rock and be there full time bitch. It started getting rough, and I reached under the bed and got out the shot gun.
I shot a load of buckshot into the middle of them. The problem is one of them died, I was found guilty of murder.
I miss my Mitt I know she is getting fucked regular because she moved up here by the prison and she comes to see me and writes me the details. Our little boy got took away from her and as for me. I have a new name here at the big house, Baby, and I loved it at first but now I have Aides and won’t live much longer.
Mitts told me good bye at her last visit and the doctor says I have a few days left at the most. I question would I change things if I could, and I have decided, it was worth it, I am only 30 but at least Mitt has all the money she will ever need and I had a full sex life. But what if, my parents never spoke to me after they found out what I was doing, no one really calls me friend, no preacher will come pray with me, and I will die alone, what if I end up in hell?
I close my eyes, I see that big cock coming toward my mouth………..the breathing gets shallow, my body grows cold, the big cock fades away……my insides burn, pain as I cough and can’t stop……..my chest oh god it hurts…..the monitor starts going beeeeeepppp………..my eyes open for the last time…..no one is there…..I go on this trip alone.
This story is fiction, I have no use for the sissy thing, but being as I have two cousins that do fit the bill I thought this seems to be something many of you do like so why not give a story a try. You can be your own judge to rather it is a hot story, or good or bad, and it is about cucking but its a bout being a gay person too. And really should not be posted on this site, but again I decided to give the story line a try.

 

[thetenndaddy]

Verey very nice story. Thanks a lot for sharing.
TennDaddy

 

[sissycuckmaid]

Here's a picture to go along with the story.

 

[tuppinsinmo]

Lol

Here's a picture to go along with the story.

Thanks sissycuckmaid, I got to give you this, your wife is hot.

 

[sissycuckmaid]

Not my wife bro.

Haven't met too many women into the crossdressing actually.