Transsexual, oral, anal, b/M Shemale
Author's Note:
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 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.
Daddy Married a Transexual
By
Wolf
A year after my mother passed away from cancer my father started leaving me in the care of a neighbor woman while he started going on dates. I was not happy with the prospect of him replacing my mother with another woman. I didn't meet more than a couple of the women he was dating.
I was quite a shock about two years after Mom passed away that Daddy brought home a big busted woman and announced that he was marrying Sophia. I instantly resented her coming between my father and me. They went on a romantic trip up the coast to Moro Bay to have a quiet wedding at a hotel on the beach with a golf course. They returned to our home Marina Del Ray. Our condo was right next to the slip where Daddy had his 25-foot sailing boat. Dad and I liked to sail over to Sana Catalina Two Harbors to enjoy the quiet weekends.
Sophia moved her personal belongings into Daddy's bedroom. What was left of Mother's stuff was given away! She brought in some cooking items and televisions. We didn't need any more TV's, I wound up getting Daddy's bedroom TV because hers' was bigger.
It was obvious that I resented her intrusion into my relationship with my daddy. Sophia did everything she could to ingratiate me to her. She did her best to cook all of my favorite dishes. Of course, I found fault with all of them, regardless if they were actually excellent. I was rude to her at every opportunity. It took about a month before she had enough.
While Daddy was at work one day and I got home from school several hours before Daddy would get home. I was in my room playing "Grand Theft Auto." Sophia came into my room uninvited and sat on the side of my bed.
"Tommy, I want to have a serious talk with you, Honey! She proclaimed.
"You're not my mother and you can't tell me what to do!"
"Tommy, I'm not trying to replace your mother! I want to be your friend."
I crossed my arms across my chest as a defiant gesture of my defiance. Sophia grew impatient with me. She said: "I know how to take care of rude boys. She grabbed me by my shoulders and forced me onto my back. I was surprised by how strong she was. She pinned me to the bed and lay on top of me, and kissed me on the mouth. I was stunned into inaction.
I was impressed by the way she kissed me. She forced her tongue into my mouth and the way she kissed me took my breath away. I was overwhelmed by the smell of her perfume. Her lips were soft and her lipstick was probably being smeared all over my face. Being kissed by a very sexy woman was exciting for a 12-year-old boy like me, even if she was my father's new wife.
Sophia started opening my shirt and kissing my chest as she worked her went down my body as she unbuttoned each button. When she got to my pants, she unbuckled my belt and unbuttoned the top button before unzipping my pants. She pulled my young cock and balls over the top of the jockey shorts waistband. I couldn't believe what she was doing. She took hold of my cock and started masturbating me. When she took my cock into her mouth and started performing oral sex on me, she was an expert at sucking cocks. She plaid with my balls while sucking me. She kept my cock in her mouth while pulling my pants and underwear down to my knees. When she completed her task, she went to work on my cock.
I had never been given a blowjob before. It was unbelievable that I was experiencing the blowjob of my life being performed by my stepmother. For some unknown reason, I couldn't cum. I was right on the edge. I was about to cry for want of an orgasm. Just when I was about to complain when Sophia started me by slipping a finger between my legs and stuck a finger to the opening of my asshole. It tickled until she slipped a finger up my asshole. It was like I was getting an enema nozzle being stuck up my ass. The strangest thing was that I started squirting cum in her mouth. She didn't miss a drop. When she finished and lifted her head and looked up at me, she asked: "Are we good now?"
"I can't believe what you just did!"
"There is so much you don't know!"
"What are you talking about?"
"There is a lot you don't know about me and your father."
I couldn't believe that she knew more about my father than I did. After all, I knew him all of my life and probably had only known him a tear or two.
Sophia sat up on the bed and tucked her long legs under her body. Then she lifted her form-fitting dress and I saw the red tight-fitting crotch of her sexy little panties. She pulled the crotch aside and reached between her legs with her right hand and when she pulled her hand out, she had a cock that was much bigger than mine in hand. The scrotum looked no bigger than mine though. She started jacking herself off until her cock was fully erect.
I sat there watching in stunned disbelief. I couldn't believe that my father was married to a stunning-looking Mexican woman with huge tits and a cock as big as my father's, between her legs. While I trying to wrap my head around that, Sophia placed her long fingers on the back of my neck and pulled my head down to her crotch. I was looking at a cock that tapered until it got to the head and the foreskin covered the head. She pulled the skin back and I saw that the head was wet and browner than the shaft. She forced me to press my mouth against the head of her cock. She rubbed my lips against the velvety feeling head until I opened my mouth and did my best to swallow her cock.
I was inspired to give her as good of a blowjob as she had given me. While I was sucking on her cock she reached under my chest and pinched my nipples and twisting them. It didn't take half as long before she came into my mouth. It was strange getting my first taste of cum from the cock of my father's new wife.
She got up, straightened up her panties after tucking her cock back between her legs and adjusted her dress. As she left my room, she looked back over her shoulder and said: "I hope we can be friends from now on."
I sat there not sure what had just happened. I was dumbfounded that evening when Daddy got home. It was like a Mayberry household. Daddy showered and changed clothes while Sophia was preparing dinner like a dutiful housewife. I was watching the domestic scene playing out, at the same time I was mentally picturing Sophia standing there naked with her tits and cock sticking out in front of her like the bumper horns on a 1955 Cadillac.
When I went to bed that night, I lay there wondering what was going in their bed. I slipped out of my bed and snuck down the hall to stand outside their bedroom and listened to the sounds coming through the door. I could recognize the sound of my father's voice as he had grunting sounds. I was trying to figure out what was going on behind the closed door. I eventually returned to bed and masturbated myself to sleep.
In the morning Daddy left for work almost an hour before I needed to get up to go to school. When it was time for me to get up Sophia came into my room to waked me up before the alarm went off. She was wearing a sexy see- through nightgown. When she woke me up with a kiss, she also reached under the covers to take hold of my cock. Her cold hand was enough to wake me up instantly. She lifted her nightgown and moved her hips close to my face and rubbed her cock against my lips. When I opened my mouth, she fucked my mouth until she fed me her cum. While I got dressed, she made me breakfast before sending me off to school with a kiss at the door.
I was distracted all day at school. I rushed home to talk to Sophia. I wanted to find out if she was going to continue sucking my cock. When I entered the front door, I went through the house looking for her. I found her in the laundry room washing the bedding sheets. After she loaded the dryer with the last load, she asked me if I would like a sandwich and a glass of orange juice. We moved into the kitchen.
I sat at the kitchen table while she made the snack for me. When she served me, she poured herself a mug of coffee and sat down next to me. She took a sip of her coffee and added a little more sugar. "I'm sure you have been thinking about what you learned about me yesterday and are full of questions about your father and me. What do you want to know?"
"Daddy has to know that you have a cock! What kind of sex do the two of you engage in?"
"Just so you know I am a transexual. That means I have been taking female hormone therapy for most of my life and to enhance the size of my breasts I have breast implants. I have been living as a woman for twenty-five years. I could have had the sex reassignment to have my penis made into a vagina years ago, but I enjoy being able to fuck other people."
I was naïve enough to ask: "How do you and Daddy fuck each other?"
Sophia smiled: "Your father and I fuck each other."
"How"
"Shall I show you how we fuck?"
I was a little puzzled as I said: "Okay."
She stood up and took me by the hand and pulled me to my feet and led me to my bedroom. The blankets were piled on the floor at the foot of the bed. I did have a desk in my room to do my homework on and build my mode cars on. Sophia looked around before she cleared my desktop and moved my desk chair aside. She sat down in my chair and unbuckled my pants and helped me remove my shoes so that she could remove my pants and underwear. She even removed my shirt and undershirt. When I was totally naked, she played with my cock for a moment before she turned my body and draped me across my desk face down. She pulled a tube of some sort of lubricant from a pocket hidden in her skirt and she lubed her cock and my asshole.
I was frightened because I knew what she was planning on doing to me.
Sophia told me: "Tommy, you have to relax your asshole or this is going to hurt. Once you learn to relax you will enjoy being fucked." She probed my asshole with a couple of fingers before she pressed the head of her cock against my asshole. It did hurt like hell. I was whining and crying but I didn't beg her to stop though she fucked until she came in my ass. When she pulled her cock out of my ass my hole was aflame and I felt liquid running down the center of my scrotum. I feared that it was blood but when I reached back and wiped my asshole with my fingers and looked at them, I saw that it was her cum on my fingers. At least that was a relief. Sophia pulled me up kissed me on the mouth before she got down on her knees on the floor of my room. She flipped her dress up over my back as she crossed her arms on the floor and rested her head on her arms. I was standing behind her admiring her ass. It was strange looking at her beautiful light-brown butt with her puckered dark brown asshole and seeing the center seam running town to divided her two-testis hanging in the sack of her scrotum and that brown cock dangling between her legs.
I knew what she was offering me without her having to say what she wanted. I approached and straddle her legs and guided my cock to the opening of her ass. Then it dawned on me that Daddy was fucking her asshole. I shoved my cock into her ass ad clung to her hips while I fucked her. At least this time her tight asshole soon had me spewing cum in her ass. When we were done Sophia straightened up her clothes and returned to doing the wash and making the beds. I was left contemplating what to place. Then I remembered noses my father had been making the other night. Then I realized that Sophia must have been fucking my father's ass. The mental picture was so strange.
That evening over dinner, Sophia mentioned that to Daddy: "Tommy has become a young man. It is time you had the talk with your son to tell him about us."
Daddy looked at the two of us: "Does Tommy know your secret?"
"Yes, he knows everything."
Daddy pushed himself back from the table and stood up. He left the room without saying anything. Sophia and I looked at each other because we had no idea what he was thinking. Sophia started gathering up the plates and putting the leftovers in containers and putting them in the fridge while filling up the dishwasher. I was still thinking about my father's reaction.
Daddy was naked when he reappeared. The only thing he was wearing was what looked like a black rubber ring that was tightly restricting the combination of his cock and his scrotum. I had no idea what that was for. I was fascinated at the sight of his cock.
I had seen his cock many times growing up but it had always been flaccid. At that moment his cock was a lot longer, thicker, and as ridged as a baseball bat. His scrotum skin was stretched tightly over his testis like a baseball. I was shocked to see him like that. Sophia let out a laugh and removed her apron.
She started the dishwasher before she unzipped the back of her dress and removed her dress. She also removed her slip and draped them over the back of her dining chair. Then she reached back and unhiked her 38-DD bra.
I was truly impressed with her tits anytime I got a chance to see those caramel-colored tits. At least when she removed her panties, I was not shocked to see her cock when she pulled it out from between the cheeks of her butt. She consciously left her nylons and pumps on. She commented that she always looks best in hosiery and pumps. The two of them pulled me to my feet and led me to the family room.
The two of them undressed me completely and they draped me over the sturdy coffee table face down. Daddy stood in front of me while he demonstrated how to put on a lubricated condom. He pointed out the need to leave plenty of room for his cum. Then he moved around behind me and he lubricated my asshole before he started fucking me. While he was fucking me, Sophia came in front of me and presented her cock for me to suck on. I was so occupied by sucking on Sophia's cock that I hardly noticed any discomfort being fucked by my father.
Sophia squirted her cum into my mouth before Daddy had an orgasm. When she pulled her cock out of my mouth, Daddy eventually pulled out of my ass and came around and stuck his cock in my mouth and told me to bit the tip of the rubber. I was able to suck the cum out of the condom after I bit a hole in the rubber. After I rested Daddy helped me put on a cock ring like his.
He explained that by wearing a cock ting that my cock would not go soft after I have an orgasm. That way I would be able to fuck for hours. I put his comments to the test by fucking Daddy and instantly fucking Sophia. I fucked their mouths as well.
I started sleeping between the two of them. It was fun having one or the other one's cock poking me in the ass. Sex became all-consuming in my life. There was a guy at school that I recognized as a guy looking at other guys with a longing in his eyes. I befriended him and he invited me to come home with him. While we were in his bedroom eating snacks, his mother made for us, he was showing me his collection of Anima comics. Then he showed me his collection of porn. I took charge at that point and started kissing him and feeling him up. He surrendered to me and allowed me to masturbate him. After he spilled his cum into a rag, I invited him to visit me.
The day he was going to visit I told Sophia that I was bringing home a classmate. When we got home, Sophia was wearing a tight-fitting dress, that showed off her figure, and her tits were almost spilling out of the dress. My guest was properly impressed with my stepmother. I told him that someday I would introduce him to my stepmother.
We went to my room and he wanted to see my porn. I told him that I didn't have any porn. I prefer to do it instead! I proceed to remove my clothes and put my cock ting on. He was fascinated but concerned that my stepmother would catch us. I assured him that we didn't need to worry bout that. I helped him take off his pants and sucked him off. He was very excited that I even swallowed his cum.
I showed him my asshole and invited him to fuck me. He was very excited and came quickly. Then I insisted that he allow me to fuck him. He tried his best to be quiet while I fucked him but he whammed like a baby the whole time my cock was in his ass. I pulled out and squirted my-cum all over his butt and rubbed it into his skin. I had him suck my cock clean before we got dressed. I still had my cock ting on when we joined Sophia and I asked her to drive him and me to his home. Before he got out of the car Sophia asked him: "Did you enjoy your visit with Tommy?"
He blushed like a child, but assured her that he had a great time. Sophia told him that he was welcome to visit me anytime and that he was welcome to stay overnight anytime we wanted.
He visited several times and we fucked each other before he asked his mother if he to spend the weekend at my house. That first night we had fucked each other before bedtime. When we were retiring at bedtime Sophia came into our room wearing a sexy see-through nightgown. My friend was so captivated by the sight of her tits he didn't notice the bulge in her panties.
He spent a lot of time at my house and was very comfortable having sex with me before we let him in on the fact that Sophia had a cock and the three of us had sex with each other regularly. He was absolutely thrilled to have sex with my father and Sophia. The four of us had a great time. He eventually came out to his parents and sought to have his name changed from Tony to Tonie.
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