Transvestite, oral, anal, FF/b, b/b
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.
Copyright 2017 Wolf, All rights reserved.
You may contact me at pomowolf74@yahoo.com if you like. All flames will be ignored.
Aunty Made Me
By
Wolf
I was born as a pretty blond boy into a household of two women. My mother was the lover of her older sister. When my Auntie decided it was time for mother to add to the family she arranged for a man she knew that was good looking to fuck my mother from behind while mother sucked on Aunties clit.
Aunty was disappointed when I was born. She would have preferred a girl. So she named me Jackie and I was raised as a girl. My blond hair was only trimmed so that it would grow long and given a soft wave. Both of them protected me flesh from the sun, because they didn't want he developing freckles. They wanted my skin to be creamy white. I was dressed as a girl. Mother home schooled me while Auntie worked.
I grew up witnessing Auntie making love to my mother, and accepted it as the normal way it should be done. I envied their breasts and pussies. I suspect that Auntie was giving me female hormones because I developed breasts and my penis remained as small as a young boy's. I was granted the privilege of servicing their pussies with my mouth whenever they wanted me to.
Auntie had a friend that was also raising a boy as a girl and thought it would be appropriate for the two of us to become lovers.
I was dressed up in a fetching gingham dress a lot like the dress worn by the girl in the story Alice in Wonderland, right down to the ankle socks and Mary Jane flat shoes. My hair was tied up with a ribbon and I had a small clutch handbag with a lace handkerchief in it and a tube of pink lipstick.
They drove me to the home of her friend, and we were greeted by an imposing woman dressed like a conservative school teacher. The blouse couldn't hide the size of her ample breasts. Her waist was cinched in by a wide leather belt with a long woolen skirt. She was wearing pumps with wide two inch heels. Her hair was pulled back into a tight dark bun on the back of her head. She kissed Mother and Auntie before bending down to hug me and kiss me on my cheek.
She made a big fuss over me. She scolded Auntie for not doing me justice. Then she escorted us into the family room to introduce us to her sissy.
She was sitting on the couch with her knees touching and turned to one side, with her hands in her lap. She was a little older than me but she was also dressed in a lace pinafore over a delicate lavender dress, with matching little slippers. Her chestnut hair was shoulder length. She had gray eyes, button nose and full lips.
She stood up to be introduced to my family and me. Her name was Alice. After the greetings the three women insisted that we get to know each other by hugging and kissing.
Alice was a head taller than me as she took me in her arms and kissed me on the mouth. It was breath taking the way she stuck her tongue into my mouth. She also placed her right hand on my butt and pulled me tightly against her body. I felt her clit poking me just above my own clit. It was obvious she had a hard-on.
Her mother cautioned Alice not to cum until she was told to do so. The three of them stood around us watching and telling us what to do. I had never had sex with another sissy, so I didn't know what to do. They had us stick our hands in each other's panties and play with each other's clit, but they kept telling us that we couldn't cum, besides I wasn't old enough too actually cum yet.
Auntie took me by the hand and led me to a glass topped coffee table and had me kneel on all fours on the table. She flipped my dress over my back and pulled my panties down to my knees. She announced, "Have you ever seen a prettier ass than this?"
The hostess approached and ran her warm hand over the cheeks of my butt and slipped her finger down the moist valley of my ass. Her finger toyed with my asshole for a moment before she continued down the seam to roll my little balls between her fingers and tug on my little clit. Then she ran the finger back up to my asshole and inserted her long finger into my ass.
If it hadn't been for a mirror over the couch I wouldn't have known that the woman had pulled out her big breasts and I felt her rub those big soft tits against my butt.
Then she stood up she called for Alice to come to me and take out her clit. Alice pulled her panties aside and took hold of her clit and jilled it as she approached me from behind. Her mother applied some sort of lubricant to my pussy and Alice's clitoris before she allowed Alice to stick her clit into my pussy.
It hurt like hell as her clit was forced into my asshole. Auntie and Mother were hugging each other and commenting on my being deflowered.
Mother, "Our little girl is no longer a virgin."
Auntie, "Dawn, don't you dare cumming, until we tell you that you can!"
Alice's mother demanded, "ALICE, DON'T YOU DARE CUM IN DAWN UNTIL I TELL YOU THAT YOU CAN!"
Alice took hold of my hips and started fucking me. I was whimpering like a baby. To muff my sobs Auntie came around to stand in front of me. She lifted her skirt and pulled her flimsy panties aside to expose her hairy cunt, and shoved her hips forward. Her big meaty pussy swallowed my face like a soft rubbery gas mask. My moans of pain were smothered by her aromatic cunt. With every thrust of Alice's hips drove my face hard against Auntie's cunt.
The women continued to demand that Alice and I not cum until we were given permission. Of course Alice couldn't continue to fuck me without it eventually causing her to cum. There came that moment when she couldn't prevent herself from cumming in my ass. She continued fucking me, but her cum started dripping out of my pussy, and dripping from my balls.
When our parents saw cum dipping onto the glass table top the three of them reacted vocally. Alice's mother started caning her butt with a bamboo cane until her butt was stripped with red marks.
When she allowed him to pull his clit out of my pussy she pulled him around in front of me and demanded that I lick her clit clean. I licked and sucked her clit until it was hard again. Auntie made me lick up the cum that had dripped onto the glass table top. Alice and I were called upon to suck their pussies. Alice sucked my mother and Auntie while I sucked her mother's pussy.
Alice's mother had a very hairy and smelly pussy. I buried my face in her cunt and sucked on her ridged clitoris vigorously until g her she had and orgasm. As soon as she started having an orgasm, she started pissing in my mouth.
As soon as I tasted the salty ammonia smelling urine I closed my mouth and she pissed all over my face. I had to close eyes until she finished emptying her bladder. Mother and Auntie had done the same this to Alice.
After we cleaned up and had dinner there was a discussion between the women about exchanging each other's sissies. Alice went home with Mother and Auntie while I was left with Alice's mother.
She carefully undressed me and put me in her tub and washed me. She used a large bath towel to dry me before taking me to her bedroom. She carefully brushed my hair and applied scented lotion to my body before putting me in her bed.
I lay there on her bed watching her undress. She was a brunette with a full figure. She had large breasts that rested on her ribcage. The sight of them was enough to make my mouth water. She had love handles on her hips and a big ass and thick thighs. Her thick bush was wedged between her legs. As she approached the bed and knelt on the bed with one knee to mount the bed I could smell her strong female aroma. She straddled my head and gathered up my hair to place it out of the way as she lowered her pussy down to my face. She rubbed her cunt against my face from chin to forehead. She extoled me to stick out my tongue, and I tasted her asshole and pussy until she let me know she was cumming.
She leaned over and pulled out the drawer of the nightstand and pulled out a strap-on dildo. I only got a quick look at it as she straightened out the straps. I was intimidated by the size of the blue latex rubber penis replica. It was about the same size as my forearm and as big around. I noticed that there was a nub on the base that would be pressed against her clitoris after she strapped it on. She had also taken out a tube of lubricant. She put a generous dollop on the dildo and used her right hand to spread he goo all over the shaft of the dildo, before she used her greasy fingers to lubricate my boy pussy. She placed a firm pillow under my butt to elevate my body, so that she could fuck me while looking at my face.
When she started shoving her dildo into my ass it hurt even more that when Alice fucked me. She slapped my face to shock me as her dildo disappeared into my ass. Then she pinched both nipples while she fucked me. Tears rolled down the sides of my head past my ears and into my hair.
She let me rest for a while before she let me suck on her tits and pussy before she fucked me doggie style. She fucked me a couple of more times before she allowed me to cuddle up against her body as we drifted off to sleep. She fucked me again in the morning before feeding me and allowing me to dress before taking me home and exchanging me for her own son.
Mom and Auntie discussed my future as if I was not even there. Auntie decided that as a sissy my education would require that I be introduced to sex with a male. She made a call and talked to someone. There was a date made for me to meet the person she had been talking to the next evening.
They dressed me up in my best party dress. I was nervous while waiting for my date to show up.
When the doorbell rang I almost panicked. the idea of a real man using me frightened me. Aunty answered the door while my mother stayed in their bedroom, because she was upset with the prospect of me no longer being the innocent girl she raised.
When Auntie escorted the gentleman into the living room I was filled with a mixture of fear and desire.
The man's name was Stuart, and he was about six-feet four. He was imposing figure. His good looks didn't prevent me from being frightened by the prospect of his fucking me.
Aunty kissed me on the cheek and told me to have a good time.
Stuart escorted me to his car and opened the door for me. He took me to a movie theater. No one gave us a second look, because it simply looked like a father and daughter were going to enjoy a movie together.
It was a family cartoon movie that was charming, but also had some sexual overtones. No one noticed that during the movie the man was playing with my clitoris through my dress. At the end of the movie we made our way to a restaurant where we had dinner before he took me to his home.
Entering a man's home was intimidating. The smell was different from home. While it was clean there was no female touch in it. He led me to the bedroom and the room was all male. I noticed that the framed photographs were of males. There were pictures of him embracing other men and even a couple of him embracing boys.
He enjoyed the fact that I looked like a pretty blonde girl, so he allowed me to remain dressed as a girl, as he placed me on his bed and removed my thin little pantie, before his kissed me and began undressing himself.
He was in pretty good shape. He was not a body builder but he only had a 36 inch waist and a 44 inch chest. He had a receding hairline and a full graying beard. What impressed me the most was that his cock was at least 8- inches long, with a thick foreskin that almost covered all of the head. I could see the purplish knob with the urethra hole. It was dangling on an arch over his scrotum that hung low with some hairs showing on the sack containing his testis. His pubic hair was dark and thick. After he finished removing all of his clothes he stood there by the bed and reached down with his right hand and hefted her scrotum up before letting it fall. Then he placed his cock between the first two fingers and waggled his cock up and down until it started becoming erect. When that big head/s eye was looking right at my face he mounted the bed.
He kissed me with toned on tongue while he played with my tits. He even suckled on my hard nipples. While he was sucking on my nipples he started playing with my little city. He eventually moved down to suck on it until I had a dry orgasm. Having prepared me he positioned me on my back with my butt on a firm pillow and he greased my boy pussy with a lubricant and his penis. He picked up my legs and placed my heels on his on his shoulders, and guided that frightening cock to my boy pussy. I thought he was going to rip my flesh apart my asshole with his cock.
I pleased with him, "Please to pull it out!"
Stuart pained no attention to my pleading and continued inserting his cock until hos pubic hair was pressing against my pubic bone and his balls was slapping mine. He fucked me while clinging to my hips pulling me against him as he thrust deep into my ass. He fucked me hard and fast. When he started to cum he pulled out and squirted gobs of white cum all over my scrotum and belly. He used his hands to rum the stuff into my skin. As I lay there feeling my asshole throb I felt the cum drying and it felt sticky and shrinking.
Stuart hugged and kissed me until I almost felt normal with his legs wrapped around my legs. When I grew bold enough to return his tongue kisses, he had me jack him off until he was hard again. Then he prepared to fuck me doggie style. It was easier on me having him fuck me that way. I even experienced a dry cum before he pulled out and squirted cum on my back and butt. After he rubbed it in he made e lay belly down until it was dry.
I felt like a sticky mess laying there while my asshole relaxed slowly. I sucked his cock several times that evening before we bathed together. The next morning after we dressed he took me home where he professed his love for me to my mother and Auntie.
They allowed me to date him several times, but weren't ready to allow me to live with a man. They enjoyed using me as their own little girl too much. I enjoyed having sex with both women and men. By the time I reached adult hood I was a sexy looking woman. I worked as a stripper and in porn movies for a living.
I lived and walked the streets as a woman without anyone fear of anyone suspecting that I had a cock tucked away. Men flirted with me all of the time, but I knew better that let a straight man discover my secret, because several of my girlfriends had been beaten up brutally when the let straight men find out they had dicks. My face was my living, so I didn't want it scared or messed up.
Mother and Auntie still enjoy having me eat their pussies and we fuck each other.
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