Date: Sun, 15 Aug 2021 17:30:33 -0700 From: Pomo Wolf Subject: Kenny's Mom (bisexual Incest, oral, anal, b/FFM) bisexual, Incest, oral, anal, b/FFM 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 adult females and males. If this type of content offends you or you are under the age of 18 do not read it. Copyright 2021 Wolf, all rights reserved. You may contact me at pomowolf74@gmail.com if you like. All flames will be ignored. Kenny's Mom By Wolf My family were originally from Arkansas but because my father was a big rig truck driver we moved to southern California because the trucking company was homebased near the Long Beach and LA harbors. The container ships bringing products relied on trucks and trains to transport goods east. We rented a modest home in the community of Carson. When Dad's dispatcher arranged for Dad to take a load going east, he also arranged for him to pick up a load for another destination and was alooking for s load coming west. Dad would be way from home for weeks at a time. That left Mom alone with me for long periods at a time. Mom married my father as soon as she graduated from high school. She gave birth to me before we moved to California. She was a very attractive blonde. Being tied down with a young infant alone for long periods at a time, in addition to the frustrations of learning to balance a bankbook and run a household. Was uncomfortable for her. She became close friends with a neighbor woman, named Ella. The woman was also a midwestern transplant. Her husband was also a truck driver that only traveled within the State, but was on the road for long periods of time as well. She was a middle-aged woman that was also sexually frustrated. Ella spent so much time at our house that she was in the habit of just letting herself in without knocking. They would sit at the breakfast table drinking coffee and discussing their financial problems and gossip about the neighbors. Eventually they discussed their sexual frustrations. One morning Ella walked in on Mother masturbating. There was an awkward moment that embarrassed both of them. The ice was broken when both of them started laughing. They admitted to each other that they masturbated regularly. Ella admitted that watching Mom finger fucking herself made her horny. She knelt in front of the chair Mom was stirring on and replaced Mom's hand with her own and masturbated her to orgasm. When Mom recovered, she pulled Ella to her feet and lifted her dress and pulled her panties down and finger fucked her. After that day when Ella came over the coffee break had to wait until they had sucked each other's pussy to orgasm. I was an only child and grew up as a Mommy' boy. When Dad would leave home Mom got in the habit of allowing me to sleep in her bed. Being a young woman with strong sexual desires it wasn't long before she began to allow me to suck on her tits. That wasn't enough and she encouraged me to masturbate her. I was able to fist fuck her. I didn't like the smell of her pussy at first. I soon learned by the smell of her pussy as she walked past me when she was horny. I would follow her and when she would sit down, I would lift her dress and lick her pussy until she would cum. By that time, she was in the habit of going without panties most of the time because if it wasn't me satisfying her it was Ella and occasionally other women. I was only 9-years-old when she left me in the care of Ella while she went to the bank and grocery shipping. She was in the habit of doing that regularly. This time Ella must have been particularly horny. She told me that she needed my help. She led me to her bedroom and asked me to pull the zipper down on the back of her dress. She turned her back to me and reached back and pulled her long brown hair over her left shoulder. I was nervous as I pulled the tab down past her waist. As the dress parted I could see that she was not wearing a bra. When she pulled the dress down, I saw that she was not wearing panties either. As she stepped out of the dress, she turned around to face me. To me a 45-year-old woman was old, but she was still a very-good looking woman. Her large breasts sagged a little and her lower tummy was soft and saggy. Her pubic bush was thick and black. Her legs were thick. I was struck by the fact that her pussy smelled so much like my mothers. She took hold of my hand and pulled me close to her and placed my hand on her left breast. She leaned over and kissed me on the mouth. I stood there feeling foolish as she felt my crotch. Without saying anything she sat on her bed and began undressing me. When I was totally naked, she took hold of my dick and pulled me closer and leaned over and took my penis into her mouth. She ducked on my penis. It felt wonderful for a while. There came a point that her pulling on my penis became painful. I didn't understand that I was too young to actually cum. She moved her body onto the middle of the bed and pulled me with her by my dick. She had me lay next to her and with one hand she lifted her right tit and with the other hand she pulled me by the back of my head to the tit. I started sucking on her nipple. She was telling me how good a boy I was for sucking on her tit good. She had me suck on both tits and when she had enough, she pushed me down and flung her leg over my body so that I was between her legs. She didn't need to tell me what she wanted. I had sucked my mother's cunt for years. I saw that her labia lips protrude past her crack a lot farther than my mother's labia did. When she pulled my head against her pussy her labia spread over my face. I couldn't breathe, because my face was pressed against her moist flesh. I dutifully sucked on her clit like Mother had taught me until she came. She was not satisfied though. She pulled me back up the bed and pulled me over on top of her. She took hold of my stiffy and stuffed it into her gaping cunt. I fucked her like I did my mother until she had another orgasm. When I pulled out of her cunt my was still stiff and wet with her fluid. Ella got on her knees and sucked my wet dick clean. When it was over and we were getting dressed, she told me not to tell my mother about what we did or she wouldn't let me do that again. It was our little secret. Mother had also told me to never tell anyone about her allowing me to make love to her. It was our little secret. Whenever Mom left me in the care of Ella, Ella made sure that I fucked her before Mom would return. About that same time Mom became involved with another woman. The first time she brought her friend home I thought she was a very pretty young woman. Her name was Leslie. Mother and I had worked out an arrangement. During the week I was allowed to sleep in her bed with her and fuck her until she was satisfied. On weekends she might bring home a woman to sleep with. On those occasions I had to sleep in my own room or spend the night with Ella. An arrangement that pleased Ella immensely. Leslie got into the habit of spending the weekends with Mother except when Dad would be home to service his rig before going back on the road. I was all of 11-ywes-old and used to seeing different women spending weekends with Mom. One of those weekends when Mom was spending it with Ella, I was spending the weekend home alone. When the doorbell rang and I opened the door I found t Leslie standing there. I informed her that Mother was spending the weekend with our neighbor Ella. Leslie said: "I would lie to get to know you better, may I visit with you then?" "I guess so." I stepped back and allowed her to enter and led her to the living room. She took me by the hand and led me to the living room sofa. She sat so close to me that our thighs were touching. She said: "I have been wanting to talk to you alone for a long time because I find you to be a very attractive young man." O was curious about him: "How did you meet my mother?" "I met your mother at a party at a mutual friend's home. The home was crowded and smoke filled and I had stepped out for a breath of fresh air. Your mother came out for the same reason. We struck up a conversation and we liked each other. We left the party because we found that the party was boring. We went to dinner for coffee and talked. When I told her that I was a transexual she was curious about how I became a trans. I proceeded to tell her all about myself. Mother indulged me and when I assured her that I wanted to be a girl, she had me talk to a doctor and I was put on a regiment of female hormones to prevent me from experiencing puberty. The therapy enhanced my natural female appearance. I even developed small breasts. I lived as a girl until I was grown, then Mother and I found a plastic surgeon that gave me a boob job to give me these beautiful breasts. I had my name changed and my birth certificate changed to female. I have been reluctant to have my penis turned into a vagina because I have been enjoying the ability to fuck men and women." I had never heard of the term transexual before, but her explanation did inform me that she had been a boy but chose to be a girl. I was fascinated by her story, and how a penis could be turned into a vagina. When she told me how it was done and when she told me how it was done, I could understand her reluctance because it sounded very painful. Leslie asked: "Now that you know about my secret, can you can still like me?" I still thought of her as a woman and was curious about her cock. I wondered if it looked like mine. Rather than say anything I just leaned over and kissed her on the mouth and placed my hand on her crotch. I was confused because I didn't feel anything down there. "Where is it?" "I keep it tucked back between my legs. I can't have it springing a boner and my giving y secret away." "Can I see it?" "Okay" She stood up and reached under her short skirt and used both hands to pull down her delicate lace panties. As soon as she stepped out of them, she reached between her legs and pulled an impressive looking cock apparently his scrotum was smaller than most and his calls were on either side of her cock when the cock was wedged between her legs. She wrapped her hand around the shaft and pulled on it until her cock was fully erect. When she removed her hand, the cock was sticking straight out in front of her body. I couldn't resist reaching out and wrapping my own hand around the shaft. I marveled at the way it felt. The skin was soft and warm over a stiff core. I was fascinated by the smell of her crotch it wasn't the same as Mother's and Ella's. I couldn't resist licking her cock. I slowly took the cock into my mouth and one I got past the gag reflex I got all of his cock into my mouth and buried my nose in her pubic hair. She eventually came into my mouth and I swallowed most of it. Enough of the white stuff leaked out of my mouth onto the matted hair that I got to see what cum looked like. My jaw ached from holding my mouth open so long. Just the same I knew that I would never refuse the chance to suck another cock. Leslie and I rarely were alone, but when I got a chance to be alone with her, I took full advantage of the opportunity. While I was sucking her cock, Leslie would finger my asshole and eventually insert a finger into my asshole. It always made me penis hard as hell. On one of those occasions, we were alone and she asked us very sweetly if she could breed me. I had never heard the term used before, but I understood what she was asking and agreed to let her do anything she wanted. Leslie produced a tube of some sort of lubricant and proceeded to cover her cock with a layer of the stuff and used her greasy finger to lubricate to grease up my asshole. She laid me on my back and place my heels on her breasts as she guided cock to my asshole. When the head of his cock stretched my hole open it hurt and I had to bite my lip to keep from begging her to stop. I endured the pain, but my own cock had a boner like no otiher I had ever had. When she finished cumming in my ass she pulled out and she sucked my cock and licked my asshole. I recovered a couple of days later and started looking forward to have sex with Leslie again. The next time Mother brought Leslie home tome have sex with they were both stumbling round drunk. I followed then into Mom's bedroom and watched them preparing to have sex with other. Leslie fucked my mother's pussy and she fell asleep shortly after he finished fucking. She rolled over onto her back. That was when she realized that I was in the room and saw it all. She smiled at me and she beckoned me to approach. I smelled Mother's cunt all over her cock when I knelt by the bed and as I leaned over her body and as I took hold of her wet cock. I licked it lean. Leslie managed to get off the bed and lay me next to my mother. She removed my pajama bottoms' and lifted my legs and proceeded to fuck me. The shaking of the bed must have disturbed my mother. She must have opened her eyes and lay there watching her trans girlfriend fucking my ass. She must have enjoyed watching the action. When Leslie finished fucking me, she sucked my cock clean before sending me back to my own bedroom. I was not surprised to see Leslie at the breakfast table. Nothing was said about what took place last night. When I got home from school that evening Mother asked me: "Dis you enjoyed what Leslie did to you last night?" "yes" "It was obvious that it was not the first time she fucked you. How long had she been fucking you?" I found out about Leslie's secret, about six months ago and she taught me about that kind of sex and I liked it." Mom thought bout it before asking: "Do you think you would like to have sex with men?" "I don't know but I would like to find out." "I think that can be arranged, Mom said. Arrangements were made for Leslie to introduce me to a friend of hers. She drove me to the home of a friend and introduced me to a man in his forties, a ginger haired man with a big smile. The man couldn't say enough nice things about me. He was very proud about his collection of antique toys. After he showed me everything in his collection, he offered Leslie and me soft drinks. We went into the living room to drink them and while Leslie sat on the couch the man led me to the leather recliner and had me sit on his lap. While I was sipping my Coke, he was running his hands all over my body. He pulled my T-shirt over my head and he used his fingers to stimulate my nipples. While he was kissing me on the mouth, he unfastened my baggy cargo shorts. Once my pants were open, he pulled my jockey shorts down and under my balls. He gently took hold of my dick and started playing with it. My little penis didn't get any bigger around but it did get a hell of a lot longer. It was more than six inches long and as hard as a rock. When he would pull it down between my legs and let go it would spring back up and slap my belly before sticking up like a flag pole. He was cradling me with his left arm while he was playing with my dick. Then he leaned down and took my cock into his mouth and started sucking on my dick. It must have been uncomfortable for him to be bent over like that. He strengthened up and removed my shoes and socks before he finished removing my shorts and underwear. When I was totally naked, he had me stand there in front of him while he proceeded to remove his shirt. Then he stood up and unfastened his trousers and pulled them off. He was wearing tight fitting little nylon jockey shorts and from the size of the bulge he had a big cock. I was impressed by the amount of ginger body hair covering his chest and belly. When he pulled his underwear down in front there was a thick patch of that ginger pubic hair and the elastic pulled the cock down until the underwear cleared his cock. It sprang back up to stand proudly in front of his body. I was fascinated by his cock. It must have been 8 or 9- inches long. It wasn't any bigger around that Leslie's cock but the mushroom head was much nigger and the scar where the foreskin has been removed t birth was a dark color. He pulled my head down to his cock and stuck it into my mouth. He only had me suck on it long enough to get it wet. He invited Leslie to come over and take his place in the recliner. She came over and she flipped up the back of her dress and sat down. She spread her legs very un-lady like and pulled the crotch of her panties aside and pulled her own cock out from between her legs. The two of them had one bend over and I placed my hand on her thighs as I started sucking on her cock. While I was busy doing that the ginger haired man placed his hand on my hips and eased his cock into my butt. He was pleased that I was able to take his cock without complaining. With every thrust of his hips drove my face into Leslie's crotch. When he finished cumming in my ass he pulled out and had me suck his cock clean. I became a frequent visitor to the home of the man with the ginger hair. I was still sleeping with Mother when dad was on the road. Ella would find excuses for me to help her. Leslie was also thrilled when om allowed her to have sex with me as long as she could watch. The arrangement continued for years. When I was a high school senior and was in the English Literature class conducted by a tall lean man that reminded me of Ichabod Crane in many ways. I was in his good graces because when he would ask questions in the class, I was the one that gave acceptable answers when we read King Lear, he asked the class why all three daughters has to die before him. I told him that there were several reasons: first the sins of the prideful insane king, the tragedy was complete when even the riotous daughter had to die, so that the king would know that with his death his bloodline would end. Things like that endeared me to him. One day I was at the student stores at the end of the school day buying something I must have thought was important, when I exited the store, I ran into my English teacher. He greeted me and mentioned that he had a book that I might enjoy reading and he would like my opinion about it. He opened his briefcase and handed me a hardbound book. The cover jacket proclaimed that it was the story of Oscar Wild. I started reading it as soon as I got home. I sat up in bed reading it until I finished reading. The next day I told the teacher I finished reading after class. He asked me to return to the classroom after the last class. When I returned, we sat down in a couple of desks next to each other in the front row. We sat there discussing the life of Oscar Wild. I could tell by his questions that he was flirting with me. I was sitting at a desk to his right that allowed me to sit facing him. At one point he got excited and placed a hand on my left knee. In response I pulled his hand up to my crotch. He paused for a moment before he squeezed my package. I reached over and placed my own hand on his thigh under the right-handed desk. He said: "Kenny I would like to invite you to my home to discuss the book where we can be more comfortable." He wrote down his address on a sheet of paper to me. As we stood up to leave, we just touched arms. I told my mother that I had a date with a horny teacher. She gave me the keys to the car and told me to be home before bedtime. I parked the car in the street in front of the house and knocked on the door. I was greeted by my teacher when the door opened. He invited me in, and I studied the living room as he closed the door. The wall facing me was a mahogany bookcase that was filled with an old-books. The room smelled of old paper and leather. There was a leather wingback chair with an end-table and a reading lamp to the right of the chair. There was an old leather sofa facing the chair. He insisted on making dinner for me and told me to have a look at his personable library while he prepared the meal. I looked at the titles of the books and even picked out a few to flip through the pages. The smell of old quality paper was strong. I was reading a few pages when the teacher returned and invited me to join him for a meal. The kitchen and dining areas were clean and looked like it came from the 1890s. When the meal was finished and the dishes were cleaned and put away, we returned to the living room. We resumed our discussion about Oscar Wild. He inquired if I had ever thought about sex with a man. I saw no reason to be coy about it. "I have had sex with a ginger haired man in his forties for the past five year. While I told him all about the sex with the ginger haired man the teacher was running his hands all over my body. I even helped him undress me. I had matured and had brown pubic hair and a five- inch cock and he admired my body after he undressed me and lovingly handled my cock and balls. He even reached under my butt and toyed with my asshole. He found that he was able to stick three fingers up my asshole. He continued finger fuckling me while he sucked my cock until my balls were dry. At the conclusion he stood up and led me to the bedroom. Again, the bedroom was also something out of an 1890s English estate right out of an old movie. The teacher was not wearing the clothes he wore at school. This afternoon he was wearing a lightweight blue silk sports shirt, tight fitting light-gray beltless slacks, and comfortable loafers. I watched him get undressed intently. He unbuttoned the shirt and removed it. He was not wearing an undershirt. He had a lean body that was not the athletic type at all, in fact he looked like the sickly type. He simply stepped out of the comfortable shoes as he was unhooking the tab of the pants and pulled down the zipper. When he started pulling down the pants it quickly became obvious that he was not wearing any underwear. The sight of his cock was a shock. I had only seen cock that size drawn on bathroom walls. It looked like it was a foot long, and his pubic hair was shaved off, although his legs were hairy. I was so engrossed in looking at him to do or say anything. He let me take a good long look before he guided me to the middle of the bed. Now it was my turn to feel his body but his cock was captivating and frightening. I didn't think it would be possible for him to stick all of that into my asshole. We spent some time kissing and masturbating each other. He encouraged me to breed him first. A task I was very familiar with after all I started fucking Mother's and Ella's asses when I was very young. He got on his knees and I mounted him doggy style. I fucked him like a bitch until I squirted my load in his ass. There was some more petting before I relatedly agreed to let him breed me. My teacher was very gentle with me as he positioned me on my back and lifted my legs up like a parent about to change the diaper on a baby. He lifted my legs up and flung my legs over his shoulders and aligned his cock with my asshole and slowly started inserting it. I expected that it would hurt but I had been fucked enough rimes that it didn't hurt any more than the ginger man's cock. He slowly inserted it. When I felt his body pressing against my butt, I realized that he had inserted all of that monster sock in me. He fucked me until he squirted his load in my colon. He informed me that the Colon is very flexible and could accommodate very long objects. I assured him that I would visit him as many times as he wanted me to. I told him that I needed to get home before bedtime. I used his bathroom to piss and take a dump. At least after that I wouldn't make my underwear wet with his cum. When I got home and got ready for bed Mom invited me to sleep with her and tell her all about my date. When she heard about the size of his cock, she wanted to meet him. The next day at school after his class I told him that my mother wants to met him. he was nervous about meeting my mother, but I assured him that om was cool with the sex. She just wants to see you breed me with that cock of yours. He reluctantly agreed to have me bring my mother that evening. He cooked dinner for three of us. Mother soon had him comfortable with, presence. I had to bring up the fact that I wanted him to breed me. When we got to his bedroom and Mother sat on a chair next to the bed, where she had a good view of him sticking that oing cock in my ass. She even masturbated the whole time. She gave me permission to spend some weekends with my teacher. In my absence, she dated Ell and Leslie more.