Date: Sun, 1 Oct 2023 10:24:12 -0700 From: Pomo Wolf Subject: Big Brother Brought Me Out (Gay/Incest, oral, anal, m/mM) Incest, oral, anal, m/mM 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 a consenting underage boy and brother and father. 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. Copyright 2021 Wolf, all rights reserved. You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored. Big Brother Brought Me Out By Wolf I was born and raised in the hill country of Oklahoma. Besides my parents I had an older brother that was just short of being four-years-older than me. My brother, David, was the jock type and girls fell all over themselves trying to get his attention. I on the other hand was small for my age and had delicate features. I often heard people say that I could have made a good-looking girl. I became fascinated with my mother's smooth and sexy underwear. When I was about 8-years-old I started taking her soiled panties out of the hamper in the bathroom. I would take them to my room and put them on. At that age her undies and bra were a little large on me but I would fill the bra with socks. Looking at myself would turn me on and I would pull my dick either over the top of her panties or one of the leg hoes and masturbate to a dry orgasm. When I was finished using her undies, I returned them to the hamper. I'm surprised that I got away with my fetish as long as I did. My brother bragged to me after a date with his first girlfriend that he had fucked her when he was 12-years old. He took pride in telling me all about his dates. He jokingly told me that I was cute and tease me about how much he would lie to fuck me. When I was about 13-years-old during the summer when Dave caught me in the backyard wearing one of Mother's swimsuits and I was masturbating with a wad of Mother's underwear wrapped around my dick. I was terribly embarrassed and tried to hide my dick and a wade of her silken undies that I was using to masturbate with. I must have looked silly in her swimsuit. Mom was not a large woman so her clothes fit me by that age. "Is that Moms bathing-suit you're wearing" was the sound of the most awesome voice I knew. It was Dave. He had come home to change after hanging out at a girlfriend's house. Apparently, she wasn't in the mood that day and he just kept looking at me. Dave said: "At first, I thought you were the neighbor girl, until I took a better look. I almost started to cry but he was not threatening or manipulating. He was very nice and asked how long I had been wearing Mom's clothes. I said for several years but they were too big until lately they started fitting better. He then floored me when he asked if I liked boys more than girls. I had to remind him that boys my age just met girls at the movies or ball games and I had kissed a few but only a few. He then asked me up front if had I had ever kissed a boy which I said no. I didn't want to ruin any friendship and no boy ever seemed interested in me. I had a best friend who was well hung for our age and I had a crush on him, but he was totally into girls only. So, I admitted it to Dave. He asked if I ever told him that I would like to be a girl at times. I said I'm already weirding you out in Mom's bathing-suit. How could I tell my best friend? Dave laughed and ran his hand over my face and before I knew it, he kissed me on the mouth. He taught me about French kissing. He played with my tiny boobs a little and told me: "If you want to learn more about what girls did, come to his room tonight after mom and dad went to sleep. Later that night I snuck into his room. He pointed me to his bathroom. I found a note that said take off your pajamas and put this on. It was one of his girlfriend's cute tops that was white with lace top and sheer and a pair of white panties. I did as I was asked, and he immediately told me: "Once I you learned how-to-put-on makeup you could be as cute as any girl in our school." He kissed me. It was so new but so different but I felt his hard cock against me. We laid on his bed and he told me how to kiss down his chest and to lick his penis like a lollipop until I got used to it. Soon I had it in my mouth. I didn't gag like I thought. He was so sweet and called me sweet names, not fag or queer, it was baby girl and sweety and how well I made him feel. He warned me he was going to explode in my mouth and I might gag but try not to get sick. It was okay to swallow or let it all fall out. I decided to go for it and tried to swallow all I could. A lot did drip out of my mouth but I didn't do too bad for my first blowjob. David sought me out after dates with his girlfriend and she didn't feel like putting out. Sometimes he would get horny and get me alone in a secluded location like a barn or a wooded area and have me give him a blowjob. It was only a matter of a couple of months before he propositioned me to allow him to fuck me. When agreed to try it he took me to a barn where he hugged me and he masturbated me until I came all over my belly and his hand. I thought we were finished but I felt a finger slide into my asshole. He had used some of the cum to slicken his finger. I was sweating profusely by the time Dave announced that he was cumming. When Dave pulled out of my ass, I simply flopped onto my belly and lay in my own sweat. I thought my asshole was bleeding when I felt liquid dripping from my asshole. I reached back and wiped my asshole and looked at my fingers and saw that it was Dave's cum dripping from my asshole. He taught me girls liked to be fingered before making love. After several minutes he rolled me over and probed my asshole with a finger coated with my own cum. After he finger-fucked my ass, until my anus was comfortable with finger in my ass, he pushed his now hard cock inside me. I wanted to scream but instead endured the pain for several minutes. Then it started feeling good then even better. I couldn't believe I was being fucked. It took him almost twenty minutes but he finally pumped a warm load into me. I truly felt like a girl. I was sore for a couple of days and vowed to never allow anyone to do that to me again. Dave was very concerned about hurting me and assuring me that he would never do that again. Of course, that promise lasted until his girlfriend crossed her legs when he wanted to mount her. I relented and allowed him to mount me. At least this time it was missionary and he jerked me off while he was fucking me. It didn't hurt as much but I did moan in pain with every thrust. Dave did kiss me after he came and continued masturbating me until I squirted cum onto my belly and his hand I don't know when my parents got wise to me being a sissy but it did become apparent. Mom and Dad had separate bedrooms because Mom couldn't sleep while listening to Dad's snoring. One evening when Mom was visiting a friend, and David was out with a new girlfriend, when it was bedtime Dad came to my bedroom and invited me to come to his room. When I lay on the bed Dad put his hand on my pajama bottoms and squeezed my cock. He masturbated me until I came before he pulled my bottoms down and rolled me over onto my belly. He stuffed a firm pillow under my waist to elevate my butt. It came as a shock when my father buried his face in the crack of my butt and licked my asshole. Then he spread my legs and knelt between my legs and assumed the doggie position and he drove his cock deep into my ass. At least David had gotten me used to a cock in my ass. Daddy hammered my butt fast and hard. At least I was prepared for the feeling of cum dripping from my asshole. When he was finished, he wiped his cock off on my butt. He kissed me and sent me back to my room. I exited his room with my pajama bottoms in hand. I had a lot to think about that night. I was still awake, pulling on my cock, when I heard Mom come in. I heard her open her bedroom door. I had a fitful night's sleep. My throbbing asshole was the only thing from convincing myself that it had all been a dream. I was the one up early the next morning and dressed and went down stairs. Mom was preparing breakfast and enlisted my help. While we were cooking the meal, she asked me: "Did you enjoy yourself last night!" I was dumb founded when I realized that my mother knew what had taken place last night. Then she added: "I have known about you wearing my underwear for some time, and that David had been fucking you. I assume that you get off wearing women's clothes, and your brother fucking you." It took me a while to process what she was saying. "You knew and didn't say anything?" "Honey, I want you to be happy with whatever turns you on. You don't need to feel guilty about liking to wear women's clothes. I love you no matter how you choose to live." "Really" "Do you want me to buy you an age-appropriate wardrobe for a girl your age and size?" "Really" "Of course, I will, your brother and father will enjoy it as well." Mom already knew all-of my measurements. She started buying me everything I needed including "Baby Doll" nightgowns. I soon had a closet full of clothes for all occasions. I could dress like an innocent school girl or go completely slutty. David had to be satisfied with fucking me before Dad got home from work, because I slept in Daddy's bed most nights. He still dated girls. I tried to keep meeting girls at the movie or pizza place, but at least once sometimes twice a week we would end up fucking in his bed or by the pool. I remember being jealous because I didn't get to go to his Junior-senior prom several months later. But his date didn't put-out, and when he came home he came to my room to get his rocks off. Mom and dad were away skiing again and he asked how quick I could put on one of mom's nicer dresses. By then I had learned to tastefully apply makeup. I thought we would end up in his room as normal but instead we drove all around. He even took me to a local drive-in for a limeade. He wanted people to see him with a pretty girl. Then we went to the lover's lane to park and he laid me in his truck, dressed up on my back and his nice cock slipped in and out of me. It was like he was hoping we got caught or someone saw his truck and told his girlfriend he had another girl parking. Whatever his motive was I did my best to be the best alternative prom date he could have wanted and let him fuck me three times that night. We got home at sunrise. I think a neighbor was a little confused but never said anything. 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.