DISCLAIMER:
This story is a work of fiction and contains descriptions of explicit sexual acts of boy's discovering their sexuality. It contains graphic scenes of sex between an 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:
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Copyright 2011 Wolf, All rights reserved.
You may contact me at whitewold999@icqmail.com if you like. All flames will be ignored.
Kansas Transvestite By Wolf
Just like the Wizard of OZ, Dorothy and I were raised in Kansas in a small town outside of Wichita. I was a small and thin, and had long naturally curly hair. A lot of times I was mistaken for a little girl. I looked so much like a girl that other boys would tease me. As the saying goes 'if I had a nickel for every time they called me a sissy I would be right today, is all too true. Anytime I wanted to pass myself off as a girl I could fool anyone.
When I was home alone I cross dressed often. Our mailman saw me both as a boy and a girl enough to know that they were both me. Harvey was in his fifties when we met. I have to admit that he was a handsome man, well built. One day when Harvey was delivering our mail, I invited him in while I was dressed in drag. He complimented me on what a pretty girl I was. I thanked him and assured him that I would love to kiss him for being so nice to me. He removed his mail bag and I practically had to jump to wrap my arms around his neck and plant a wet kiss on his mouth.
Harvey wrapped his muscular arms around my waist as I wrapped my legs around his waist. I loved the feeling of his beard stubble on my face as we stuck our tongues into each other's mouth. The only thing separating my butt from his cock was the thin girl's nylon panties and the thickness of his underwear and the thickness of his U.S. Mail uniform pants. I swear I could feel his boner poking me right between the asshole and my scrotum. When we broke our kiss, I slid to the floor in front of him. I unzipped his pants and pulled out his cock, while he stroked my hair, and told me what a sweet girl I was. When I saw his cock I thought it was very large. (I learned later that it was just average sized.) As I approached his cock I could smell those wool blend pants, his freshly washed underwear and the many body odors of his cock and balls. His cock was circumcised and his mushroom head had a thick purple roll around it. I took the knob into my mouth and relished the velvety feeling in my mouth. Harvey used both hands on the back of my head to pull my face against his open pants. His cock actually touched the back of my throat. I almost threw up as a result of that. I was in heaven while he actually fucked my mouth. When he shot his load into my mouth, I swallowed it as fast as I could. Some cum seeped out at the corners of my mouth. When he pulled his cock out of my mouth I wiped my mouth with the back of my hand. I looked forward to every time Harvey could stop by long enough to feed me some cock.
It was about three months before he fucked me. It nearly drove me nuts waiting for him to get around to it, but when he finally did the stars came out The first time Harvey fucked me, was one of the times I went to his home in full drag. We were wrestling around on the floor of his living room. I had on a full skirt and petticoats, blouse and bra (ala 1950's), and my hair was pulled back into a curly ponytail. There was no fear that anyone seeing me on the street would suspect that I had a cock under my skirt. While we were playfully rolling around on the floor he was constantly trying to get his hand under my skirt, and of course I was resisting him like a proper young woman would. There was no way I could overpower him. I could feel his hands all over my legs. Every now and then his hand would brush against the bulge in my tight fitting little low rise panties. I tried to resist him grabbing my goodies. My breath was coming in gasps and was labored. Sexually I was on fire, very horny and wanted him to do more to me.
Finally his fingers reached my boy pussy. He pulled the crotch of my panties aside and tickled my asshole for a long time. One finger played with the entrance of my asshole. I soon felt something warm and greasy, and I knew he was putting some kind of jelly in the entrance to my asshole. I turned my head so that we could kiss. I even sucked on his tongue to ensure him that I was enjoying what he was doing to my asshole. I was moaning my approval while wiggling my boy pussy around to encourage him to stick his finger deeper into my ass. It did hurt a little, but I wanted more of it, so I did everything I could to drive my butt down onto his finger.
I begged him to fuck me! "Please fuck me now, Harvey! I want to feel you inside of me so bad I can taste it! Please fuck me now!" He was reluctant to try, because he feared that he would hurt me so badly that it would require medical attention. A trip to the emergency room would result in our relationship being known. But he finally relented and rolled me onto my stomach and pushed up my skirt, and virtually ripped my panties off of me. He greased me up some more. I felt his cock head touch my boy pussy. I nearly died when I felt him slowly insert it, but it wouldn't go in all of the way the first time, but eventually his full weight was resting on top of my back and it popped in. Then he started fucking me like a truck driver on a cheap diner whore.
The second man I had sex with was named Lenard. He was equally as handsome as Harvey, and I discovered that he was endowed even better. He was younger, in his mid forties. I met him while fishing one day, and we hit it off right away. He saw me sitting alone on the bank of the creek, and just sat down next to me after asking if he could join me. I loved the earthy smell about him. We talked while we dangled our lines in the creek. He didn't come on to me at first, and I was not sure if he was my kind of man. He joined me a couple of more time on the bank of the creek, before he invited me to visit his home.
My folks were pleased to allow me to visit over night with him after meeting him. I suspect they knew just what my relationship with him was all about, and trusted him to protect me from physical harm.
One day he invited me to his house, and it was not very far away from my parent's home. I went to his home on a Saturday afternoon. He lived alone just outside of town. While we talked for awhile he asked me if I wanted something to drink. Of course I accepted. I told him that I would like one of his beers. Being only 12-years-old one beer went to my head quickly. I began to tell him my secret desires. I told him all about my desire to dress up like a girl. I told him how I managed to sneak some of my sisters underwear and clothes from the clothesline. She thought they had blown away or she misplaced them. I complained that I didn't get to dress in her clothes as I wanted too.
At that point he suggested that I bring them to his house, and he would allow me to dress up whenever I visited him I agreed right away. I knew right away that he was interested in more than just friendship with a boy that looked like a girl. He must have suspected that I was a sissy by the way I looked. It wasn't long before I was in his arms being kissed and fondled. There was no way that he knew I had on girl's panties under my jeans. Anyway the first time I was in his house he placed his hand on my knee. When I didn't reject his touch he leaned over and kissed me on the mouth. I loved the way he kissed me and worked me over. While we were kissing he was feeling me up. I felt his manly chest before I placed my hand right on the bulge in his pants. He started taking my clothes off, and I even helped him take off all of my clothes. He was very excited when he saw my panties, but what he was more interested in was what my little dick looked like. He rolled my dick between his fingers and pressing my balls gently. I could hardly contain my excitement the way he worked me over. He sucked my little cock and balls, while he loosened up my asshole with his fingers. When he got me to straddle his hips by standing on his chair facing him, I was more than happy to sit on his erect cock. It was much larger than Harvey's, and stretched my asshole to what I thought was the limit. I loved being fucked by him.
He did a lot of things for me. One time he took me to a party where the other older men brought their young male lovers. I should say there were only three other men and their boys. That was sure an experience.
We played a game called 'Know the Cock.' They put a sheet up with a hole and the adult men stood behind the curtain and stuck their cocks through the hole in turn. The other boys and I were to pick out our lover's cock. I can proudly say I won because Lenard had a little red dot on one side of his cock. The party was held at Lenard's house.
That night we played several kinds of games, and we even changed partners, which turned out to be an enjoyable experience, I have to admit that I was a little jealous. The other little girly-boys were cuties also.
At the time Lenard would bring me gifts. While I was inspecting the gifts he would allow his hands to linger on my body. That always made me feel funny inside, like I was becoming very special to him. One evening while visiting Lenard, he took me to a drive-in movie while I was dressed as Joni Kay. As soon as we parked and it got dark we moved to the back seat, because there was more room to do things. It wasn't long after the movie started that I had Lenard's cock out and in my mouth, sucking and savoring his pre-cum. I looked up from his lap and said "Fuck me!" I felt him reaching under my skirt and pulling my panties down my thighs so that he could put some lubricant in my boy-pussy. When he was ready I turned my back to him and lay on my side to expose my pussy to him. He rolled over and guided his cock into my ass. He fucked me with long slow even strokes until the rhythm increased until his cock exploded in my ass. That was a thrilling adventure, because we could have been discovered at any time.
Another time I got dressed up as Joni Kay for a ride in the country. While we were passing a farm we happened upon the sight of a bull mounting a cow in a green pasture. Lenard parked the car under a shade tree while we watched the sight of the bull fucking the cow. We got out of the car to watch the action. Lenard draped me over the fender of the car, with my skirt over my back and my panties down around my knees. He fucked me right on the spot. Harvey and fucked in more times and in more different places.
One of the most memorable events was a trip to Colorado. We stayed in a little village near Colorado Springs called Black Forest. The place was located out in the country in a secluded location. On the way there Lenard and I stayed the night in Garden City Kansas to rest up before the final leg of the trip. I enjoyed the trip because I was dressed as Joni Kay. I enjoyed flashing truck drivers during the trip. I would pull up my skirt and put my feet on the top of the dash. One time I looked up at a truck driver and spread my legs for his benefit. Lenard was getting worked up over all of my flashing, and he took it out on my boy-pussy that night in Garden City. We stayed near a place called Black Forest. Those were two weeks I'll never forget. I never had so much cum, and been fucked as I did during that time.
I recall one incident in which I both got fucked and sucked a hard cock by a couple of other cross-dressers. I was in the reading lounge of a home we were staying in and I was lying on the floor looking at a magazine when a black haired cutie, named Lori, came in. We engaged in some small talk, and then she dropped down near me and wanted to look at what I was reading. She was really close and I could smell her perfume. It was stimulated by her smell, and I moved a little closer to her. She put her hand near my waist and began a movement around by my butt cheeks. I let out a soft moan, and she said, "Oh sorry!" I smiled and gave her a little peck on the lips. She looked into my eyes and soon our lips were at each other and our tongues searching the inner part of our mouths. I felt her hand go under my skirt searching for my boy pussy, and looked to stick her finger inside.
I asked, "Do you have any gel?"
She found a tube on the table, and she soon had me lubricated.
"Oh GAWD...Fuck ME NOW, Please fuck me now!" I pleaded.
I didn't notice a blonde cutie that happened to walk in, because I was concentrating on the dark haired one sticking her long cock into my ass. Lori had rolled me onto my stomach and lifted my shirt and petticoats, and pulled down my tight lace panties. She lifted her own skirt and held it up while pulling down her own panties in preparation for sticking her cock into my boy-pussy. She began to fuck me slowly, that was when I noticed the blonde. I motioned for her to come close, and ran my hand up her leg under her skirt. I found an impressive cock restrained by fancy little panties.
The blonde lay down in front of me, while pulling up her skirt to her waist. I reached for her stiff stem, and after getting it out of her panties I licked and kissed it, until she moved her hips towards me as an offer for me to suck on it. I took all of her cock into my mouth and started sucking like mad.
GAWD! What a way to start the day. Having cocks in both of my ends.
Later I fucked the blonde in the barn. Man what a good fuck she was, she didn't want to quit. I fucked her ass twice and then stuck my cock her mouth. She sucked my cock clean before we adjusted our panties and lowered our skirts.
While we were traveling on to Denver, I was even fucked in the van. Lenard was also very understanding about all of this, and he was caught up in fucking the other cuties too. It was very exciting to sit on someone's lap, and to get fucked in the ass while cars and trucks passed by. It was a wonder we never got caught by some State Trooper along the way.
I told him that I was his fuck muffin now and forever. He even bought me a new wardrobe befitting the little whore I was for him. My favorite was a slip with matching bra and white garter belt and panties. Harvey loved to fuck me while I was dressed up in them. I would kiss his cock before and after he fucked me with all of the love I could bestow on him. When I would get dressed up in a school uniform I would twirl around in my petticoats letting him see my lace panties, so that he could take note of my hard cock. He would sit me on his lap and pull my skirt up, so that his cock would rest in my pussy's crack. GAWD I loved that feeling. One day while he was playing with my ass, he took my boy pussy, and made it his. It had been awhile since Harvey had penetrated me, so it hurt at first. When I got used to the size of his cock, I couldn't get enough of it. I also became adept at sucking his cock without losing any of his cum. We were lovers for about five years, until his death. I was heartbroken until I found another older man that took me under his wing to become his little slut.
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 whitewold999@icqmail.com