TV oral anal, m/MMM
This story is a work of fiction and contains descriptions of explicit sexual acts between a consenting youth and adult males. If this type of content offends you or you are under the age of 18 do not read it.
If you enjoy Nifty, please make your donation to Nifty Archive Alliance to help keep the site running and stories available.
You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored.
Sean Becomes Amy
By
Wolf
I had two sisters who helped me become Amy. They caught me wearing their panties and started dressing me up in their clothes. It was easy enough because we were close to the same size. I was only twelve at the time. They taught me how-to put-on lipstick and eyeliner. The biggest change came when I went on a date with my older sister. She wanted to take me on a date with a guy, so that she could watch how it would go.
I was dressed in a skirt and blouse with all the accessories. She instructed me to do everything she told me. Her date was a football player, and mine was a friend of his. They were sixteen and I was thirteen. I was small for my age, and she told them I was a virgin and they could not fuck me, but oral would be okay. That scared me. I had never done anything like that before. We were driven into the park in an old four door Chevy sedan and my date started kissing me in the back seat. My sister was in the front seat making out with the football player. My date took his cock out and tasked me to suck his cock.
I took his cock in my mouth and started sucking on the head of his cock. I loved the feeling of his satin smooth mushroomed head in my mouth and started working the shaft into my mouth while sucking on the throbbing flesh. His hand was on the back of my head and he pushed my head down onto the shaft of his cock until the head of his cock hit the back of my throat and I gagged. I struggled to keep sucking his cock, and I was enjoying myself sucking on a cock of a guy that thought I was a girl.
He kept encouraging me, and my sister and her date were watching me sucking the cock of my date. I loved sucking on his cock, and when he breathily announced that he was about to cum. I lifted my head up until only the mushroomed head was in my mouth as his cock throbbed as he squirted cum into my mouth. I swallowed his cum and kept sucking until his cock went limp.
My sister's boyfriend wanted me to suck him and got out of the front seat and changed places with his friend. He got in the back seat with me. His cock was bigger, and I sucked on the head, enjoying the smooth feeling and the taste. I sucked his cock as deep as I could gagging a little.
The idea of the fact that they didn't know that I had a little cock tucked back between the cheeks of my butt, and was cumming into my panties as I sucked the cum out of his cock. It felt so good I did not want to stop. I loved sucking on the head and after he came, I swallowed his cum. He let me lick and suck on his balls. My sister was telling us what to do.
She told the football player to pull his pants down and get on his knees with his head resting on the rear deck so that her little sister could rim his asshole. I got on my knees straddling the driveshaft well and clung to his big muscular butt as I started licking his asshole, while she and the other guy were watching me tongue fucking the asshole of the football player.
His cock and scrotum were dangling between his legs and his cock was getting hard again, and she told me to also lick and suck his balls and cock from behind.
I liked everything that was taking place and licked his balls and ass while stroking his cock. I held his cock up to take it into my mouth before he squirted his second load of cum into my mouth. The best was when I swallowed his cum again.
When he was finished, he struggled to pull up his underwear and jeans before opened the back door and got out to finish fastening his jeans before he changed places with his friend again, when he was back behind the steering wheel next to my older sister, and his buddy was back in the back seat with me. I sucked the other guy again. I sucked his balls while sucking his cock. He lasted longer this time, and I was able to suck him for a long time. He loved me rimming his asshole and I licked him as deep as I could. I loved all the sex
My sister changed places with me and allowed both guys to fuck her wet cunt and lick her cum filed cunt before having them take us home.
After the success of that night, I started getting dressed up in my sister's clothes and going to the park to meet guys in the park and suck them off. I got away with that for a long time before the man I had picked up wasn't satisfied with me just sucking him off. He wanted to fuck me. When he forced me down on the ground and pulled my delicate panties off my legs, he saw my little penis flip up from between my legs. He was surprised to find out that I was not a girl. His face went from anger to a wicked grin as he knelt between my legs and drove a thick cock into my asshole. The pain was extreme and I was crying and pleading for him to quit.
My prostrations were load enough to draw a crowd of adult men that encouraged the man to fuck the crybaby sissy. When he was finished, he turned me over onto my belly and pulled me up to my hands and knees and he encouraged the onlookers to fuck my ass doggie style. I lost count of how many men fucked my asshole before they allowed me to pull up my sister's panties. I waddled home in a lot of pain. I feared the cold liquid flowing down the insides of my legs blood. I snuck into the house and made my way up the stairs gingerly. I sought out my older sister and she almost panicked when she saw me. Her dress was a wrinkled grass-stained mess and I was limping like I was in a lot of pain. She helped me to the bathroom.
While I started taking off her clothes, she drew a warm bath for me. She helped me get into the tub. At least my fears that my asshole was bleeding was relieved to see that it was just cum leaking out of my asshole. While I was soaking in the tub, she set about helping me bathe, before she checked out the damage to her clothes. She also helped me get out of the tub and dried my body. She helped me get to my room and into bed before returning to the bathroom to drain the tub and clean up after me.
I was sore as hell for several days afterwards. One day while walking home from school as I was passing the home of a widower that he was a British immigrant and liked his British accent.
He called out to me: "Sean, I have noticed that you have been limping for a couple of days. Is there something wrong?"
I was embarrassed that I had not been able to hide the pain of walking. I tried to pass it off with just a sprained ankle, but he was concerned and asked me to come in and he would brew me a cupper of tea. I tried to play it off, but he insisted and ushered me into his home. He led me to the kitchen and while I gingerly sat at the kitchen table, while he put the kettle on the stove. I watched him perform a little ritual of brewing tea: he filled a teapot with hot water and brought cups and saucers to the table along with a platter of cookies that he referred to as crumpets. He put the loose tea leaves in a metal strainer and poured the water over the strainer and pressed them to squeeze the aromatic juice into the cups. He offered me cream and sugar. I had never used cream in tea before and only used sugar. He doctored his cup with both cream and sugar.
While we were sipping our tea, he asked me the truth about what had happened to me. He said: "A few nights ago I saw you waddling home wearing a rumpled dress." There was no rancor in his voice, just genuine concern.
I broke down and told him about enjoying getting dressed up in my sister's clothes and sucking male cocks. Then I told him all about the man raping me when he discovered that I was a boy, and my pleading for him to stop attracting a crowd of men that cheered him on. When he was finished. I lost count of how many other men fucked me. When I told my oldest sister bathed me and put me to bed.
He was very compassionate about my plight. He assured me that anal sex needn't be all that traumatic. It can be very pleasurable if done right.
He asked me if I would like him to have a look at my bum, because he had an ointment that could reduce the sting.
I felt his compassion and trusted him, so I agreed to let him have a look at my asshole. While I was taking down my pants and underwear, he left the kitchen long enough to return with a tin containing a white salve. He had me drape myself face down over the table and he gently spread the cheeks of my butt and he checked out my inflamed sphincter. Then he used his finger to scoop up some of the salve and gingelly applied it to my tinder flesh.
There was an instant cooling effect that felt good. He told me not to move so that he could apply more salve as needed. While I lay there, I soon had a boner. The man saw mt dick twitching and he took hold of it and proceeded to masturbate me until I squirted my-cum on the kitchen floor. When I was finished cumming, he applied more salve to my asshole. The cooling effect was instant and my asshole felt a lot better.
The man was very gentle as he prepared to breed my ass. He pulled down his own pants and boxer shorts and even applied some of that salve to his cock before he gently pressed the head of his cock against my asshole. I was able to relax my asshole by stringing like I was taking a dump. His cock invaded my colon. I could tell when he had it all in my ass when I felt his pubic bone pressing against my butt. When he started fucking my ass, I felt his balls slapping against the bottom of my own balls. He took his time fucking me. He was in no hurry, but when his orgasm approached the speed of his pumping action increased until he suddenly stopped moving and pressed his body hard against my butt. I knew he was pumping his cum into my ass.
When his cock slipped out of my ass, I was almost euphoric. There was no pain in my ass. I turned around and went to my knees and sucked his cock clean.
When I got home, I told my sisters all about what our neighbor had done for me. They gave me clothes to store at his home, so that I could get dressed in drag before having sex with him. We had a five-year loving relationship before I moved on to expand my contacts with other men
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@gmail.com
If you enjoy Nifty, please make your donation to Nifty Archive Alliance to help keep the site running and stories available.