DISCLAIMER:
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.
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Copyright 2015 Wolf, All rights reserved.
You may contact me at pomowolf74@yahoo.com if you like. All flames will be ignored.
Mother's Sissy Girl
By
Wolf
My parents were defiantly members of a special group of sexually uninhibited families. My mother wasn't satisfied that I wasn't born a girl, so she raised me to be a girl from the start. I was born with her good looks; auburn hair, blue eyes, dimples on both cheeks. My father was a handsome man with no body hair on his chest and legs, which was a blessing when it came to raising me as a girl.
They named me Jackie, when I was born at home. They deliberately registered my sex as female, because they had planned from the start to see to it that I was a female in everything except the scrotum and cock that were between my legs.
I was dressed as a girl in every respect. Mother let my hair grown until it was down to the middle of my back. I was taken to the beauty parlor with my mother regularly and the women there fussing over the darling little girl. My hair was encouraged to develop a natural wave. Mother didn't like bangs, so my hair was simply parted in the middle and pulled back, and I had a natural widow's peak. Mother chose to show off my widow's peak. I enjoyed seen my reflection in the mirror, because I took pride in looking like an attractive girl.
I received a variety of female hormones injections and pills to insure that I would develop female features even before reaching puberty. Daddy treated me like an adorable girl as I grew up. Both mother and father played with my penis, while referring to my penis as my clit. I was breast fed until I was 8-years-old. My family belonged to a social group that was also raising their boys to be sissies.
We were home schooled and were dressed as girls. My classmates and I were encouraged to have sex with each other. Our teachers rewarded us for excellence, by either jacking us off or sucking our penises. We were even allowed to suck each other's clits, and were instructed in ways to relax our sphincters to allow our classmates to fuck our assholes.
Eventually my parents parted ways, so I became one of the many boys raised by a single parent. I never saw my father again, but that didn't stop my mother from teaching me to please men as a sissy boy-girl. She allowed me to entertain men in her presence.
She turned out to be a dominatrix. She has a good figure, and I'm sure, now, that she had breast enlargements because I don't know of anyone with a size 6 figure having G sized breasts. She would entertain both women and men dressed in dresses made of leather or PVC. Many times she would have on corsets that supported her breasts from underneath without covering up her breasts, and wearing huge dildos strapped to her body. She enjoyed fucking me in the presence of her guests.
When other boys were developing muscles and starting to sprout hair under their arms, above the penises, and on their faces, I was growing noticeable breasts. I was even slow developing any pubic hair. Mother insisted on me shaving my under arms, legs and above my clit. My scrotum didn't drop like other teens, but my cock did grow to a respectable five inch uncircumcised thing. I was still being fed a variety of pills, and shots that were female hormones.
Mother enjoyed watching me suck on women's tits, while their husbands fucked my asshole. Having two men visit so that I could suck cock while being fucked. I loved being used by strong handsome men, even though it was embarrassing being used in front of other women.
When my mother felt like enjoying the company of women she would arrange for me to have a sleepover with one or more of my fellow classmates. Sometimes the fathers of the other sissy boys would join us in bed. It was exciting sucking on the tits of other sissies while their fathers hammered my asshole with large cocks.
One such evenings I was sent to the home of one particular delicate young sissy that was new to the school. I had not met his parents, so I had no idea what to expect. When I was dropped off and approached the front door decked out in a charming pink pinafore, with Mary-Jane shoes with lace ankle socks. Anyone happening to witness my arrival would simply assume that a nice looking girl had arrived. My hair was hanging down my back.
When I knocked on the door I was greeted by my classmate dressed in only a see through blouse. She was sporting a three inch uncircumcised clit and tight little balls. She greeted me with a hug and a kiss, before leading me into the family room. Her father placed his arm around the sissy's shoulders as she introduced me to her father.
The man was about six feet tall, naked, sporting a seven inch boner standing tall, and with a pot belly and was covered with dark hair. He had fat man tits that were hairy. His large face had a goatee with mustache. His eyes were dark brown, with thick eyebrows, and a receding hairline. He was a frightening looking man. He looked like he had been in a lot of fights, because his nose was bent over to the right side of his face like he had received a right hook. His eyebrows were scared, and there was possibly a knife scare on his belly. He looked like the kind of man that could be violent. He was just the kind of dangerous of man I was attracted to.
He motioned for me to approach them. As soon as I was within arms-reach he pulled me against his manly smelling body. His sissy was standing to his side with his legs wrapped around his father's left thigh. The boy's little penis was pressed against his father's thigh.
I wondered how such a delicate little boy could be the product of this man's loins. I wondered about his mother, and that was answered when she entered the room.
She was a delicate thing with long hair. She had a tray with four glasses on it and a shaker of something alcoholic. All she had on was a little black apron with white lace for a border. The bottom of the apron didn't cover her crotch. Her hairy vulva was plainly visible. Both of her 36-C breasts were also visible. She presented the drinks to us. Even her son and I got a glass.
The drink was sweet but very strong. When we had emptied the shaker the glasses and tray were set on a cocktail table, and the father pushed his sons head and mine against the mother's tits. We started sucking on her nipples greedily.
The father stood behind us, and flipped my dress over my backs, and pulled my lace panties down to my knees. Then he took hold of his sons and my clit. He jacked us off. We were still sucking on his mother's tits while the man took turns stuffing his fat cock in our assholes. I must say taking that fat cock in my ass was painful enough, but he was brutal the way he fucked me.
Many times Mother would have parties with other dominant women. They would bring their own sissies for training in dressing and behaving properly with women. They would be dressed in age appropriate dresses. They would have us hug and kiss while we played with each other's clits. While we jacking each other, our mothers would be threatening us, not to cum until they gave us permission. When we failed and spilled cum before we were told they would punish us. They would be standing there commenting on our performance. Eventually Mother would have me lie face down on the bed with my skirt up and panties down, so that the other sissy could lay on top of me with his clit stuffed in my boy-pussy. Mom was asking me, "Do you feel like proper girl?"
I would respond with a simple yes.
The other woman would be make comments like, "Don't you think they are charming the way they are developing a deep attachment for each other!"
From the age of 14 to 18 Mother allowed me to date older men. My wardrobe included sexy dresses for such occasions. Our favorite dress was simple black sheath, with black three inch pumps. On such dates I wore self-supporting nylons and a simple matching pearl ear rings and neckless. My penis was hidden under tight fitting panties that hid my penis completely. A lot of times I was taken to parties where no one suspected that I was anything but an attractive girl.
I was thrilled to have other men flirting with me while we danced. After the party my date would take me to a secluded location where we wouldn't be disturbed, and he would push the driver's seat back as far as it would go before unfastening his pants. More often than not they would have large uncircumcised cocks. They would grab a hand full of my hair, and pull my head down to their laps. I was very skilled at sucking cocks. I would suck their cocks until they would cum in my mouth.
When they would bring me home Mother would invite them to spend the night with me. She would send me off to get ready for bed. When I would return I would be in a delicate baby doll nightgown. My little clit would be sticking out in front of me for my date to admire.
They would take me to bed and fuck me. Some like to do it doggie style, while others like to do it missionary style, because they like to play with my clit until I would cum all over my belly.
Mother also became friends with a 50 year old nun that had a taste for forbidden sex. She was drawn to my mother's dominate traits. Mother would get decked out in leather or PVC and spank the nun's bare ass, before making the nun eat her pussy. Mother would make the nun suck on my tits, while playing with my clit. When I would cum Mother would make the nun lick up the cum. The nun enjoyed fucking me with a dildo, and having me fuck her in her pussy or asshole too. Mother was also planning my marriage.
She handpicked a man that was thirty years old to be my husband when I was eighteen. He was a wealthy man that had a taste for sissies. Like my mother he liked to watch other men use me. I enjoyed too please him in the same way I did everything to please my mother. Many a night, he would sit in his favorite chair naked while I would cling to his thighs while sucking his cock. He would have a friend of his fuck my sissy pussy from behind. I loved the smell of their manly sweaty body, while they used me.
I only weighed 125 pounds as an adult, and when I walked the streets no one would ever suspect that I had a cock between my legs. I enjoyed the lascivious looks I got from both men and women. I even picked up women that thought I was a lesbian. I would make love to them, without letting them touch my crotch. I would allow them to suck my breasts. When I was ready I would surprise them by fucking them with my sissy clit. Other times I would pick up horny men, and bring them home to meet my husband.
I would strip the men and suck their cocks, and allow them to suck my tits, but not let them touch my crotch. Eventually I was sit in front of them and pull my clit out of my panties, and stick it in their mouth. Some men would get mad to discover that I was a sissy, while others would willingly take my clit into their mouths and suck me off.
In either case my husband would be there to protect me. Even the one that got mad would be restrained, while he would fuck their assholes. They would be whimpering and begging, but eventually would suck my clit dry.
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