DISCLAIMER:
Gay/TV. Oral, anal, Dom, b/FFf, b/bbbMMM
This story is a work of fiction and contains descriptions of explicit sexual acts of boys and men discovering their sexuality. It contains graphic scenes of sex between consenting underage boy and adult males... If this type of content offends you or you are under the age of 18 do not read it.
Author's Note:
This story is the property of the author. It can be downloaded for personal reading pleasure or sending to a friend, but if you wish to re-post them at your own site, please contact the author for permission.
If it is illegal to read such material where you live or if you find the topic distasteful the please leave now. If you enjoy the story or if it evokes memories of your own, please let me know. I am happy to write stories from outlines.
Copyright 2015 Wolf, All rights reserved.
You may contact me at pomowolf74@yahoo.com if you like. All flames will be ignored.
Making a Sissy
By
Wolf
My mother couldn't be called the nurturing type at all. She was an alcoholic drug addict. At least she didn't become an addict until after I was born. Without benefit of even knowing who my father was. She had given me the name Francis. As far as I know I was conceived as a result of a drunken encounter in a bar. By the time I was five years old she was not a responsible person to raising a child, so her sister given custody of me by the court system when they found me wondering the streets naked, and found her passed out on drugs. One of the men she brought home had raped me while she was passed out.
My aunt was named Ruth, and she had a daughter that was a teenager, named Mary. She also had a husband that was named Danny. Ruth had her husband totally pussy whipped.
As soon as I was put under her care my life changed completely. Ruth and Mary were both very nice looking women, where her husband was a much older man with a pronounced overhanging pot belly, and a receding hairline, along with a graying beard.
It was a radical change to be given three meals a day. I was given new clothes to wear. They welcomed me into their family as their child, and I was taught to call Ruth Mother, and her husband Father. She had my named changed to Francis Harris to make me a true member of her family. They made a fuss about how much I looked like a sweet little girl.
Mary even found some of her old clothes that were my size, and dressed me in them. She showed me off to the family, and they were pleased with what a charming girl I made. My hair rarely had ever been cut, so they allowed my hair to grow, and they styled it like a girls. I was so pleased with the adulation I received from my new family that I was happy to dress as a girl all of the time. My wardrobe became completely feminine. Being a young boy my penis and scrotum was small enough to be contained in little girl's panties. When they took me out in public everyone assumed that I was a five year old girl. Rather than putting me in public school they found a home school group to put me in.
The group had all of the boys were cross dressing and the girls were cross dressing too. They felt it would be best to have me in a group that would accept me. I was the sweetheart of the class. Everyone couldn't complement my family enough. At that age sex was not important to me, even though my parents and sister handled my penis and balls a lot. I even got little bones when they handled them. Mary suggested that they by a device to restrain them, so that my boner wouldn't give-away that I was a boy. I only had to wear it in public, because they enjoyed seeing my boner tenting out the front of my skirts and dresses.
All of them enjoyed giving me baths and playing with my penis and asshole. They were not modest at all. They paraded around in the nude a lot. I was even permitted to suck on Ruth's and Mary's tits. They showed me what their pussies looked like too. As part of my sexual education Ruth allowed me to watch Dan fuck her in both her pussy and asshole. Ruth encouraged me to suck Dan's cock in front of her and Mary. They assured me that someday they would let Daddy fuck me.
Mary encouraged me to watch her masturbate with dildos. She let me use her small butt plugs to stretch my asshole. Ruth and Mary always reminded me that if I was going to live as a girl, I should marry a man that would bread me in the butt. I was thrilled at the prospect of eventually having a man fuck me.
My favorite photograph was the one where Ruth, Mary and I dressed up like Civil Way southern Bells all decked out with bustles, hooped skirts, with the tops pushing up our breasts until they looked like they would pop over the top of the dress. Our waists were in girdles that synched in our waist to the point that we could hardly breathe. The picture was taken at a costume garden party, where I was a big hit. All of the ladies had to lift my skirt to check out that I was a boy. I was wearing ruffled pantaloons that went down to my ankles, but the crotch was cut out, so that ladies could play with my little penis. I had a lot of lipstick smeared all around the base of penis that day. I went to many such parties in period costumes. The roaring twenties were fun too.
When I had my ninth birthday party all of the families from our home school group were invited. The boys were all decked out in their best party dressed and the girls were dressed up in sports coat, slacks and ties. After cake and ice cream I was allowed to open my presents. I received some very attractive dresses to add to my wardrobe. Mommy made a big announcement that as part of my birthday Daddy was going to deflower me. The guests applauded as Daddy led me off to the bedroom.
Daddy undressed me of my party dress and placed me on the bed. I lay there watching him removing all of his clothes. I was very familiar with Dan's body, and I hoped I would never become as hairy and fat as him, but I was fascinated with his hairy balls and his cock.
I had seen him fuck Mommy in the ass many times in the missionary position, so I lay there with my legs spread waiting for him to mount me. When he got on the bed he lifted my legs up and placed my heels on his shoulders, as he guided his cock into my asshole. He was telling me what a pleasure it was to bread me for the first time. Even though I had stretched my asshole with a variety of butt plugs it still hurt when his cock entered my asshole. I did my best to not cry out, but I did a lot of whimper while he fucked me. We were both sweating by the time he shot his load in my ass. When he pulled his cock out of my ass he moved up the bed and stuck his cock in my mouth for me to clean it. When we got dressed he told me not to put my panties on.
When we emerged from the bedroom we were greeted my more applause from the gathering. I could feel cum dripping out of my asshole, and dripping on the floor or running down the inside of my thighs. All of the males both boys and men had to play with my penis and asshole. The women also check out my boy pussy, and tugged on my little penis.
Mommy told me that now that I was a true pussy girl I could go on dates with the men. There was a lot of commotion over which man would be my first date. Nothing was decided at that time. Mother wanted to pick my first date herself after everyone left, so there wouldn't be a big fuss.
I wanted a very handsome father of one of the younger girls. He didn't have any boys, so I figured he would be very appreciative of a date with me. Mother agreed with me, and set up the date.
Mommy dropped me off at the home one evening and I had a bag with my nightgown and everything I would need to get dressed the next day for school in the morning. I was greeted by his wife and my classmate. She was a full figured sized 16 woman, and her daughter was destined to be just like her. The woman was dressed in a simple house dress that buttoned down the front, and my classmate was a 13- year-old, and she was dressed in a sports shirt and baggy pants. I'm sure she had her breasts strapped down to enhance her male look. Mommy and I were treated to tea, while we waited for the husband to get home from work.
While we were sitting in the family room Mommy and I were sitting directly across from the couch shared by the mother and daughter. It was obvious that the woman was not wearing panties. Mother assured them that they should feel free to do anything they wanted while we waited for her husband.
My classmate was named Roberta, but preferred Rob. She gave us a wicked smile before turned to her mother and kissed her on the cheek, as she placed her hand on her mother's thigh and ran her hand under the dress and started masturbating her mother. They put on a good show for our benefit. It was interesting to watch a teenage dyke getting all over a full figure woman. As she lay back and allowed her daughter to eat her pussy before producing a strap-on dildo to fuck her mother with.
When the husband got home from work, he was pleased to welcome Mother and me. Mother turned me over to him, and followed Rob and her mother to a bedroom. The man took me to his bedroom, where he had me sit on the bed while he removed his clothes. When he approached me his body smelled of a male's sweaty pungent-ness. Just smelling him gave me a raging hard-on that tented up my dress.
One of the reasons Mother and I chose him was because he was a blond with an even skin tone. When he was naked his body was almost hairless, except for the light brown pubic hair above his cock and underarms. I was impressed with the size of his flaccid cock as he approached me he was stroking his cock, and it came to a full erection in his hand. It was sticking out in front of his body parallel to the floor. He was circumcised, and his knob was large with a round purple head. The scar where his foreskin had been cut away was whiter than the thick shaft.
I had put on my Baby Doll nightgown without the bottoms and was lying on the bed on my back. My little boner was quivering at full erection under the transparent nightie. My heart was pounding as he lay on the bed next to me.
He was shaved closely, so making out with him was like kissing a woman. While he was sucking on my tongue, he was playing with my penis. I took hold of his cock and squeezed and pulled on his cock until he was ready to fuck me. I assumed the missionary position again as he mounted me much like Daddy had done to me. It was much easier being fucked the second time. I only grunted with a little pain while he fucked me. I was very pleased with myself when he shot his load in my ass. When he pulled out he flopped on his back next to me, so I leaned over and sucked his cock clean for him. When he was ready he surprised me by not only sucking my cock for me, he also licked my asshole lean.
We emerged from the bedroom to get a drink of water. He was naked and I was still in my Baby Doll. His wife, daughter and my mother were in the kitchen having finished with their threesome. Mom was dressed and kissed me on the cheek and told me to have a good time. After she left we returned to his bedroom. He fucked me again, and afterwards I he spooned me as we drifted off to sleep with his arms wrapped around me.
In the morning he fucked me again before we showered and got dressed. His wife had made breakfast for the four of us. He went off to work as usual, and very pleased with himself. She cleaned up and took her daughter and I off to our home school class.
While her daughter and I were in the back seat she wanted to know how it felt being fucked by her father. I assured her that I loved it. She told me that she had fucked her mother again last night too.
At school that day all of my classmates wanted to know all about my date. Even the dykes were curious about it. The woman teacher took me aside during the rest period and had me suck on her tits while she jacked me off.
The next big event in my life came when I was 12- years-old. By that time I had dated all of the men in the home school group and even dated some of the older boy/girls. Mom got a thrill out of watching me all dressed up in my school clothes hugging and kissing another teenager all dressed up as a girl. She encouraged us to play with each other's cocks while we kissed. She demanded that we not cum until she told us to. Of course we never could hold out that long, and would wind up squirting cum all over each other's dresses. That would lead to us getting bare bottomed spankings.
When Dad and Mom had proof that I was old enough to cum, they agreed that it was time I was taken to the club as it was called. Dad drove me to a secluded farm house in the county. There were several cars parked in front when we got there. When we entered there were at least a dozen men there and each one had at least one transvestite boys all dressed up like girls. Some were dressed like young school girls, and the older teenagers were dressed in tight fitting cocktail dresses. The men were and interesting lot.
Most of them were fat old men with big beer bellies, a few of them were still in good shape. Some looked like outdoorsmen with full beards. Others looked like business men. As they undressed several of the men were wearing lace women's panties though. That night I was fucked by every man there and more than a few of the teenagers. I sucked so many cocks I thought my jaw was going to lock in the open position forever.
The funny thing was, I never wanted to have a sex change operation. When I grew up I became a female impersonator in a review. People couldn't believe I was a man because my figure is more like a woman's, and I have size 36-DD breasts without visible breast implant scars. The last thing I do with every performance is to pull my restraining G string aside and show off my six inch cock and scrotum.
My manager is t husband, and I enjoy a full sex life with him. Sometimes I cheat on him when I'm attracted to a good looking man. I have even been paid to have sex with women that get off having sex with a woman that has a dick to fuck them with.
If you enjoyed the story and have a story you want me to write about your introduction to the world of male sexuality, please send your outline to pomowolf74@yahoo.com