The Making of a Transvestite - Cover

The Making of a Transvestite

Copyright© 2016 by unclemick

Chapter 1

Incest Sex Story: Chapter 1 - A son thinks he's gay and through a series of events, transforms into his true calling.

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   mt/Fa   Ma/Ma   Ma/mt   Mult   Consensual   Gay   BiSexual   Heterosexual   CrossDressing   Shemale   True Story   Cheating   Cuckold   Slut Wife   Incest   Mother   Son   Brother   Father   Daughter   Uncle   Nephew   Grand Parent   DomSub   Humiliation   Rough   Gang Bang   Group Sex   Orgy   Black Male   White Male   White Female   Anal Sex   Analingus   Bestiality   Cream Pie   Double Penetration   Masturbation   Oral Sex   Big Breasts   Hairy  

I learned a few things early in life, 1. My mom was an incestuous slut. 2. I was very feminine. 3. I was gay. 4. I loved older mens cocks. And 5. I had a big dick myself.

My mom, dad and me, lived on my grandpa’s farm with him and my moms three older brothers. My uncle John gets his son, Billy, every other weekend and were more like brothers than cousins. Dad worked in that little town as a used car salesman. Grandpa was 65 but in very good shape, while my mom, dad, and her three brother’s were all in their 50’s. My grandpa and all of my uncles were, big, hairy men with big hairy bellies and my mom was the youngest, at 54. Her name is Mary and she was very pretty and had a good body for her age. She wears her brown hair in a ponytail and has thick glasses that she can’t see without. She’s only 5 feet tall but has big boobs and a perfect round bubble butt. I’ve spied on her when she was dressing and know she has a very hairy, brown bush covering, almost her whole lower belly. I’ve seen my dads big cut cock many times when he would take me to the restroom.

My name is Andrew but I go by Andy, and I was a freshman in high school. I got teased and picked on a lot, for being so feminine and a couple of times, guys even made me suck their dicks. I never told anyone because I loved it and it made me curious about older mens cocks. My cousin Billy was a year older than me and a lot more experienced in sexual matters. We hung out together whenever he visited. Theres a small park, close to the farm with a basketball court where me and Billy would shoot hoops. I’m not very athletic like Billy but I have fun doing it.

One weekend when Billy was coming over, he said he would get his mom to drop him off at the park. I walked on over to the park and waited for over an hour. There were restrooms at the park so I decided to take a poop. When I walked into the men’s room, I noticed a long urinal on the wall with 2 older men using it. The commodes were in stalls behind the men but there were no doors on them. I felt a little embarrassed but I dropped my pants and sat down anyway. I thought I’d wait until they left before I did my business but they were taking their own sweet time. As I looked at them, I noticed they were both stroking their cocks and admiring each others. A couple of times, they glanced back at me. The guy nearest the door, turned sideways and began feverishly jacking his big hard cock toward the other man. Within seconds he started to groan loudly and his big cock began squirting long strings of his hot, white, cum all over the floor. Then he shook his softening cock off and left.

The other big guy had turned sideways to watch so I was looking at his even bigger cock, straining to shoot its load. He turned it toward me and walked a few steps and asked in a feverish tone, “ain’t you Mary’s son, Andy”. I shook my head yes and he moved very close to me as he kept pumping his cock. Then he asked “do you want to suck it”? I must of looked at him questioningly because he said, “I just thought, you know, your kind of girly and your mom’s the way she is, you know what I mean, don’t you”. Then he moaned “Oh God, I’m close, please suck it, your mom loves sucking it, Oh God I’m gonna cum” and upon hearing that, I leaned forward and engulfed about half of his, hot, hard, throbbing cock into my mouth and sucked as hard as I could. As he humped my mouth, his big cock began to jerk and churn out load after load of hot, salty, sticky, thick cum. He filled my mouth, three times and said “thank you” and left.

He bumped into my cousin Billy on his way out. Billy had watched me suck the man and had pulled his own big cock out and was now stroking it right in my face. His hands pulled my head toward it and God, did I want it. I swallowed his whole cock, even though it gagged me. I kept on until I could do it without gagging and it dawned on me, my own cousins big beautiful cock is fucking my throat. Billy was now, trying to gag me but he couldn’t hold out long enough. He began chanting “suck it Andy, suck it good, oh yeah, that’s it, oh yeah, here it cums Andy, ahhhh, oh god, ahhhhh, oh yeahhhhhhh, thats sooo goooood, oh God, FUCK that was good, God your better at it than your mom”. In all, Billies big cock must of pumped out about half of a measuring cup of hot, sweet, slimy, delicious cum. When it was over, I asked Billy “why does everybody bring up my mom”? He said “wow dude, I thought you knew”. I asked “know what”? He said, “well Andy, your moms a nymphomaniac, she’s fucked every man in this town and some of the surrounding towns, I hate to be the one to tell you all this but you would of found out anyway”. I said “and you’ve fucked her too”. He said “by everybody in town, I meant, me, my dad and all of her brothers and even grandpa”.

I was blown away, Billy even told me about a room upstairs where the family fucked her. He showed me a peep hole in the room next to it, where you could watch. I asked Billy if my dad knew and he said “yeah but he don’t like it none and your mom said she would quit doing it, so he forgave her”. He also said “now, nobody fucks her until your dads at work”. Billy was a horn dog so I wound up sucking his nice cock 4 times that weekend. We also watched my mom fuck grandpa and all her brothers those two days because my dad had to work weekends. Grandpa and my uncles all have big cocks, that I hoped to suck someday. I would still go to the park every day and the old guys all knew me and I’d get to suck at least one cock per visit.

Me and uncle John cleaned the stalls and fed the animals every morning and evening. One such evening, we were finishing up our cleaning and I was on my knees scattering hay when uncle John pointed to the pony next to me. I looked over and hanging a foot from my face was a black, fat, 14 inch long, rock hard, pony cock. My uncle grinned and said “I think he likes you Andy and you can’t just leave him like that”. I asked “what can I do about it”? Uncle John said “you can stroke it for him, he cums quick and he’ll love you forever”. I looked again and my uncle said “go ahead, just use both hands like you were jackin yourself off”. I took a hold of the ponies cock with one hand and tried to pull it to me but it was too hard, to go far. I turned and wrapped both hands around it and began stroking up and down. The pony whinnied and looked around at me as his big cock jerked and swung wildly. He was getting restless and he was humping my hands. My uncle hollered “he’s gonna cum Andy, put your mouth on it”. I thought about it as I noticed my uncle stroking his own big cock that was sticking straight out. Without thinking about it any more, I locked my mouth onto the first four or five inches of the ponies hard cock and licked the big flat head of it. The pony must of loved it because he started shooting ounces of his hot, watery horse cum into my stretched mouth and down my willing throat. There was so much cum that, my belly felt too full when it was over. I kept licking and sucking until the big cock drew back up into its sheath.

My uncle moaned, “damn that was hot”, as he stroked his own big, drooling, cock. I walked on my knees over to him and as my mouth locked on to his cock, his big hands locked onto my head and he just fed me more horny cock. He was rubbing my head when he asked “are you gonna swallow” and as I nodded yes, he just grunted and jerked every time his big cock pumped a big load down my throat. His cum was thick and tasty and it clung in big globs to my tongue and the roof of my mouth. Soon he was trying to push my mouth off of his tender cock. When I finally released it, he said “damn that was good, do you mind if I tell daddy and my brothers about this”. I said “hell no, tell em all, I want more of this family cock”.

Over the next two weeks, each of my uncles caught me by myself and wound up feeding me their big cocks and hot cum. Grandpa took me to the barn and just dropped his overalls, unleashing the biggest cock in the family. I worshiped his big cock slowly and then I licked and sucked his big balls and then he rewarded me with big globs of his hot, thick, salty, family cum. I was sucking a nice big cock every day and I loved it but as they say, “all good things must end”. One day, my dad came home early and caught my mom fucking grandpa and me sucking uncle David’s big cock. He packed some clothes, loaded me in the car, and him and I moved to Ohio. He never mentioned what he saw.

Dad’s brother lives there and he had offered my dad a job and a place to live. When we got there, it was a run down two story building. The bottom floor was an adult bookstore with peep show booths and an adult theater. The upstairs had a big appartment for us and the rest was storage. We got moved in and my dads new job was to run the bookstore. He had to work from 8 am until 10 pm, 7 days a week. I didn’t know anybody and I was horny as hell. It was summertime so I was also bored with a lot of time on my hands. About a week after we got there, I started snooping around and found a side door under the steps to the apartment. After snooping some more, I found that the door, opened inward and I could slip the lock with a piece of thin metal. Once inside, I shut the door and it locked again. I found a light switch and turned it on and discovered this was another storage area. Across the room, I saw another door so I made my way over to it. I opened it slowly and peeked inside and saw that it was a rest room with another door going somewhere else. I went in it and closed the door behind me. I decided to pee before going any further and just as I pulled my dick out, the other door opened and an older man said “sorry, I didn’t know anyone was in here” and shut it again. I finished peeing and opened that door and peeked inside. This room was very dark and had a movie screen showing porn.

I slipped inside the theater and just stood there, looking around. I was in the very back of the theater where there were couch’s along the wall. After my eyes adjusted, I made my way to the end of a couch and sat down. I could see about 10 people scattered around the big room, some together, some roaming around. After a minute or so, an older man came and stood by where I was sitting. I thought he looked like the guy from the restroom but I wasn’t sure. He kept looking down at me and after a while, he began rubbing himself through his pants. I could tell his cock was pretty big by the length his hand moved up and down on it. As he rubbed his cock with his left hand, he rubbed the back of his other hand over my cheek. He then turned his body to me and started rubbing my cheeks and mouth with both hands. I was horny and wanted to touch his cock but I was scared. He slid his middle finger in my mouth and began finger fucking it. His finger was salty so I began to suck on it as I reached up and squeezed his big cock. We continued this way until he undid his pants and let them fall down to his ankles. Now I was stroking a fat, 8 inch cock that was hot and as hard as a rock. I was also rubbing his big balls with my other hand. He unbuttoned his shirt, exposing his big hairy belly and I thought, God, there’s nothing sexier than a big hard cock sticking straight out under a fat round belly.

His cock was only inches from my mouth and we both kept inching forward, until it was time for me to open my mouth and welcome his big drooling cock in. He smelled good and his cock was big and very hard and hot in my mouth. As I slowly sucked him, it was more like we were making love. Periodically, his cock would release more salty pre-cum that I would savor. Other men gathered around to watch and stroke their own cocks. The man gently took hold of my head and guided it up and down on his wonderful big dick. He began to push his belly toward me as he whispered, “do you want to swallow my cum”. I eagerly nodded yes and he went off. His cock swelled and jerked just before it erupted his scalding hot, salty, tasty thick cum into my mouth and down my throat. He finally pushed it all the way down my throat and moaned and jerked until his big balls were empty. After a minute, he pulled out and leaned down and kissed me on the mouth.

I’d never kissed another man but I liked it and I liked him. As he zipped up and left, I noticed four more older men, stroking their cocks as they looked at me. I began sucking them, one by one, starting with a big black one. He was well built with about a ten inch, fat, uncut dark black, shiny dick with big low hanging hot balls. His cum was thick and hot and just kept spurting down my throat. After I’d sucked two more guys and was enjoying sucking the last one, a bright light was shined in my face just as the man began to force his big, hot, cum pumping cock, down my throat. The light was my dad doing a theater check and I was glad my face had been smashed into the mans crotch. When the mans cock was happy, I snuck out the way I came in.

When I stepped into the bright daylight, it took a moment for my eyes to adjust. When they did, I saw the first man I’d sucked motioning me to his car. When I walked over to him, he asked “do you want to go to my house and suck my roommates huge cock, he’s big black and always horny”. I had nothing better to do so I said “hell yeah” and we left. When we got there, he said his name was John and his friends name was Leon. Leon walked around me as if he was inspecting me and when he was satisfied, he began to rub my ass. His hands were big and rough and he touched me all over, also very roughly. He told me to strip, and I liked the way he was dominating me. As I stripped, so did he and hanging between his legs was truly a “big black cock”. It was uncut and at least 10 inches long with a big mushroom head that was already dripping cum. His big hairy balls were a perfect match to his huge cock. He told me to bend over and when I complied, he began to rub my ass and tease my asshole with his fingers. He hollered to his friend, “bring me that little black dress and a medium length black wig”. While waiting, he squirted something cold between my ass cheeks and then buried his big finger deep in my virgin ass, making me scream in pain. He said, “try to relax your ass” as he assaulted it with his finger.

John came in with a bra, crotchless panties, a dark wig and the little black dress. Leon told John to dress me as he pushed two big fingers into my ass. The next thing you know, I was wearing a sexy black bra as John began helping me get into the dress with Leon’s finger, still buried in my ass. He put the wig on me and brushed it out of my eyes as Leon kept up his relentless assault on my ass. I was beginning to like the feeling of my ass being fucked and my own big cock was beginning to get hard. John told Leon to give me a rest while he put lipstick on me. When John finished dressing me, he brought a full length standing mirror and put it in front of us. As I looked at myself, I was blown away at how pretty I was. Leon whistled and said “damn bitch, you look good” and then he pulled his fingers out and touched my asshole with the tip of his big cock. I was watching him in the mirror as he grabbed my hips and began pushing his massive cock into my ass.

My legs locked in pain and I couldn’t move my lower body. Leon pushed about half of his big cock in me and stopped. He said “relax and it won’t hurt so much”. After a minute or so, he began to slowly fuck me. It hurt but it also felt really good as he fed me more and more of his wonderful big cock. By now, I could see John’s cock tenting his pants. I whispered to him, “can I suck it” and he just stripped and walked up to my face and fed me his nice big cock. Here I was, a 10 inch black cock hammering my ass and a 50 year old mans big cock fucking all the way into my throat as he stretched my mouth wide open. They were both talking about fucking this hot slut as they fucked me faster and faster. I felt like I was going to pass out when my own cock started pumping hot cum all over John’s hairy legs. At the same time, I felt Leon bury his big cock, that began to jerk and fill my ass with his hot, wet cum. As he moaned in pleasure, John pulled my head down hard on his spasming big cock and let it erupt into my sucking mouth. His cum was thick and very salty and just kept pumping as he grunted like a big bull.

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