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I have a story to tell about an unusual situation in my family. I hope it doesn’t offend or upset anyone. It seems completely natural and acceptable to me, but you be the judge.
I have a Brother named Earl, and he is three years older than I am. My name is Kathleen, but when I was a little girl everyone called me Kitty.
Earl and I were very close when we were kids. Of course, he was into boy things, and I liked to play with my dollhouse. He had a lot of friends, and I had mine too, although not as many.
Earl was still living at home, even though he was twenty-one. He had taken some classes at the community college, and he was looking for a decent job so he could be on his own.
One of Earl’s constant companions was a guy named Robert. They hung out almost every day. Robert was a small, delicate young man, and very effeminate, although I did not know what that meant when I was eighteen years old.
I did know he was different, he wasn’t rough-and-tumble like all the other guys. I also noticed that he seemed strangely affectionate with Earl. He would stand very close to him, and sometimes touch him in a tender way. Again, at my age, I didn’t know the ramifications of his behavior.
One day while I was reading in my room, I heard Earl and Robert talking in Earl’s room. Our rooms were close together, with just a small hallway between them. The door to Earl’s room was missing.
It was a mystery to me then, but I later learned that Earl was caught masturbating by our Mother several times. They removed his bedroom door as a kind of punishment, and to remove his privacy. They wanted him to know that he could be caught easily. It was to break him of what they thought was his bad habit of masturbating. They might as well have tried to break him of his habit of breathing.
I overheard Robert say, “I bet you can’t get that big thing in me. It gets bigger every time I see it.” I was very curious to know what he was talking about, so I quietly walked down the hall to Earl’s door. I peeked around the open door frame, and saw Earl sitting in his chair, and Robert sitting on Earls’ bed.
Earl had his penis out, and was stroking it. It was very long and stiff, and I had never seen it like that. I had seen him getting out of the shower and so on, but it was very different now. Earl was well developed, at twenty-one he was at the peak of a mans sexual abilities.
Robert said, “Please don’t waste it. Give it to me.” Earl answered “I thought you just said I couldn’t get it in you.” Robert said, “I know it didn’t work last time, but I will make sure it does now.”
The head of Earl’s bed was against the far wall. Robert unbuckled his belt and pulled his jeans and underwear down to his ankles. He got on the bed face down, and Earl climbed on the bed behind him. They were both facing the other way, so I could move out more into the doorway for a better view.
Robert reached back and spread his butt open, and Earl moved closer and put his penis up against Robert’s butt-hole. He started to push, and it went in little by little. I had very little knowledge about sex at that age, but I knew that this was a very dirty and very exciting thing to do.
Robert just held still with his eyes closed, and Earl began to slide his penis in and out of him. I was transfixed. Earl went faster and faster, and suddenly he grunted and stopped. Robert made a muffled noise and lifted his butt up against Earl. I was amazed that Earl could get his very long penis all the way up Robert’s behind.
Robert said, “God, Earl, your prick is so big! You just squirted jism in me!” I had never even heard the word “prick” and of course now everyone says cock. My head was spinning, and I went back to my room, and hid out of view behind my door. I was careful to not make any noise, because I did not want them to know that I had observed them.
For the rest of that summer, whenever Mom was not home, they were in Earl’s room. I watched them many times from his doorway. I would wait until I knew they were on the bed together. Now they would get completely naked, and Earl would hump away on Robert with wild abandon. I started to feel a strange tingling in my pussy when I watched them.
Before winter came, Robert moved to another city. Earl’s strange sex life came to an end. I could hear him masturbating in his bed at night, and that excited me.
About a year passed, and now I was masturbating in my bed too. I could hear Earl doing it in his room, and it excited me. The images of Earl fucking Robert played in my head like a movie. I would tickle my pussy, which was now hot and wet, and I would have an orgasm at about the same time as I heard Earl have his.
Earl got a full time job at a manufacturing plant. He moved out to his own apartment, and my masturbation casino oyna became a solo instead of the duet it had been. By then, my fantasy was getting richer with added details. I no longer viewed the two of them from the doorway, in my mind I moved closer to the bed, right behind them. My imagination was working overtime.
My knowledge of sex had increased quite a bit by then. I had given a guy a hand job in the park one night. I stroked his cock like I had seen Earl do it, and when he came, it squirted all over me. Thick, creamy cum pumped out of his cock. I had been comparing it to Earl’s cock, and it was about half the size.
Now I knew what happened when a man finished. So I knew that when I had seen Earl suddenly stop, and Robert got very excited, that Earl was squirting his cum into him. I added this to the erotic movie that played in my head when I masturbated.
I was not too interested in guys my age. I had a few dates, but nothing happened. I was constantly dreaming and fantasizing about my big Brother.
When I was nineteen, I finally realized and admitted to myself that I had an overpowering urge to have sex with my Brother. I hope this doesn’t disgust you, but I couldn’t help myself. I couldn’t get the images out of my head of him fucking the girlish Robert in his asshole.
By that time, my fantasy had become more detailed and graphic. I imagined that I was right behind them, very close. I could see Robert’s pinkish brown asshole as he spread himself for Earl. I watched as Earl put the tip of his cock up against it, and pushed.
My vivid imagination had Robert squirming and whimpering as Earl’s big cock slid up his asshole. Robert’s hands would go limp at his side, and Earl’s cock would disappear into the crack of his butt as it slid in and out. Earl would grunt and groan and I would visualize the streams of cum shooting into Robert’s stomach. Then I would explode with my own orgasm.
From the time I was nineteen to the present, I replaced Robert in the fantasy. I took his place in Earl’s bedroom, and asked Earl to fuck me. I was the one lying still with my hands spreading my butt. I was the one who felt the tip of Earl’s cock touch my asshole.
I was the one who squirmed and whimpered as he pushed it up in me. My hands went limp at my side, and I felt him slide it in and out rhythmically. I imagined the feeling of his warm cum spurting into me. That would bring me to an orgasm.
I doubt that any other girl had a richer, more erotic fantasy life.
Now to the present day, and my dark and dirty secret. I am twenty, and of course Earl is twenty-three. I had made a commitment to myself to make my fantasy come true.
At twenty, my body was pretty mature. I had nice long legs, a slender firm butt, narrow waist, and small but pretty breasts. I was much prettier than Robert was.
To illustrate just how obsessed I became, I wanted to make sure I looked OK down there. Of course, I had never actually seen my own asshole.
I got into an awkward position on my bed, on my back with my legs up in the air. I used a hand mirror to inspect my asshole. There is no hair or dark discolored skin around it. It is just a nice little pink hole.
I explored it a little with my middle finger, and it felt good. I carefully pushed my finger in, and I visualized Earl’s cock going into me. I fucked myself with my finger, wishing it was his cock. It was fascinating to watch my finger slide in and out of my asshole. I actually had an orgasm without even touching my clit.
I desperately wanted to believe that Earl would be willing to penetrate and inseminate me anally.
I have had sex with a couple of my boyfriends, but it was always in the backseat of a car parked in a dark place. Just a quick in and out of my vagina, and a wet feeling. I wanted a lot more than that.
Earl now has his job and his own small apartment, and I visit him there often. I can’t stop thinking about sex with him. I imagine myself in Robert’s place, with Earl’s big cock up my ass. I keep telling myself that it is wrong, and unacceptable, but I can’t help it.
One late evening, after more than a few beers, we were talking about our childhood days. I steered the conversation to his friend Robert. Earl said he had no contact with him for the last two years. He did have a wistful expression on his face as he thought about Robert. I said, “He was very special to you, wasn’t he? You two were very close.”
Earl replied “I am not sure what you mean.” Come on, I said, you know what I mean. “I watched you make love to him many times. He was more like a girl than I am!”
He was devastated. He said, “I am not gay! I have never done that with anyone since then. Robert was very intelligent, and very persuasive. He talked me into it! He canlı casino goaded, coerced, and challenged me to do it. I finally gave in!”
I said I knew that, and I knew he was not into gay sex any more. But I also said, “It was very hot. It made me excited to watch you. I know you enjoyed fucking him.”
I probably should not have said it that way; he got very red in the face.
I told him about my fantasies in great and vivid detail. I made him blush. But I held back on the final version, where I had replaced Robert, until the very last.
Earl said, “So you watched us from my bedroom door?” I replied yes, a dozen times or more.
“I watched as you shoved your cock up Robert’s feminine butt. I watched as you slid it in and out, and then you would cum in him.”
“When I was eighteen, I didn’t understand what happened when you finished. I just knew you were done, and I had to get out of there before you caught me.”
“When I was older, I understood how the cum shoots out of a cock, and I knew that you were pumping your cum up Robert’s ass.”
“I played and re-played the scene when I masturbated, and when I reached the part where you came, I did too.”
“It became an uncontrollable obsession. When I turned nineteen, it changed. I didn’t plan it or intend it, but suddenly Robert was out of the picture.”
Earl looked puzzled. “What do you mean? What happened/”
“All of sudden, it was me lying on the bed under you. It was me you were fucking. It was like an out-of–body experience, because I was watching myself being fucked by you.”
“I could kind of move around and fly and zoom like a camera. I could get up close behind us, or I could go directly overhead. I watched in my imagination from every angle as your cock went up my asshole.”
He said “My God, Kitty. I am so sorry.” He had a look of shame on his face.
I said, “Don’t be sorry. When I played the movie in my head after that, I had orgasms so intense I was afraid I would wake the whole house up.”
“It was weird, because the woman you were on top of was definitely me, but it was me that was watching, too. She was me, but a slightly different me.”
“I started to think of the person I was watching as Roberta, since I had replaced Robert. That way, I thought you would enjoy fucking me as much as you enjoyed fucking Robert.”
He angrily said “I have only fucked women since then, and there have been a lot of them!”
I said I knew that too, and then I shocked him. I said, “I would like to be one of them.”
He was speechless for a minute. Then he said “Kitty, we can’t do that. You are my Sister!” I thought it was interesting that he used my little girl nickname.
“Kitty, I just don’t think I can do it.”
I answered “Don’t call me Kitty. Call me Roberta.”
That did it. I saw the look of shame disappear, and it was replaced with lust. I said, “No one will ever know but you and me.”
I think I was as persuasive as Robert had been. I could see his cock making a bulge in his pants.
He said “My God, I had no idea you felt that way about me.”
“Do you really want me to do it?”
I said I sure do, right here and now. I went over to where he was sitting, and I unbuckled his belt. I unzipped his pants, and he helped me pull them off. Next came his underwear, and his cock was right in my face. I took it in my hand, and started to stroke it. As I felt it grow in my hand, I said, “Robert was right. It does get bigger all the time.”
I took it in my mouth, and gave him a slow blowjob for a few minutes. I could only get about half of it in my mouth, so I made a ring with my thumb and index finger, and stroked the rest of it. I had an urge to make him cum in my mouth, but I wanted it up my ass even more.
I was red hot now, finally knowing I was going to get my wish. I took all of my clothes off right in front of him. Seeing that, he took the rest of his clothes off too, and he got up and led me towards his bedroom.
We got into bed, and as I stroked his stiff cock, he played with my very wet pussy. I reminded him that we couldn’t do it that way, he would have to pretend that I was Roberta. He said, “I don’t need that fantasy. I know who you are!”
I remembered what I had heard Robert say to get what he wanted that first time, so many years ago. I held his cock gently, and I said, “I bet you can’t get this big thing all the way up my ass!” The challenge worked, and he replied “I bet I can!”
He had some sexual lube in the drawer by his bed, and I asked him why. He said that with a cock the size of his, it was helpful even for vaginal sex. He applied a generous amount to my asshole, and pushed his finger in to make sure.
He slid his big, long finger in and out of my asshole, and my temperature kaçak casino went up higher. I was quivering with anticipation, waiting for his cock to go in me. I didn’t have to wait long.
He turned me over on my stomach, and he got on top of me with his legs outside of mine. I spread my butt like I had seen Robert do so many times, and I felt his cock touch my asshole. He pushed the head in, and I flinched and gasped.
He was surprised, and he said “Haven’t you ever done this?”
I said no; I have been waiting for you. The only cock I want in me is yours.
Knowing that, he proceeded gently. He eased it into me, and I took deep breaths as it stretched and filled me. When I finally felt his balls touch my butt, I knew it was all the way in. I had an involuntary spasm or reflex, and my asshole clenched up on his cock several times. He said, “Please do that when I start coming. “
Everything I had imagined came true. The steady, rhythmic in and out. The feeling of complete surrender. The tight ring at the entrance of my ass had been stretched, but now it just relaxed and accepted his cock. I continued to make whimpering noises as the head of his cock reached my stomach.
Even my powerful imagination could not match the feeling of his long cock sliding up my asshole. I had not expected it to reach that far up in me.
He fucked me for as long as he could, and then he shot a huge load into me. I remembered to squeeze his cock as he came, and we were both in ecstasy.
I stayed the rest of the night with him, and we did it twice more. The next morning, over coffee, we agreed to see each other often. We also agreed to only have anal sex, because we had convinced ourselves that it was OK that way.
He gave me a key to his apartment, and I would go there as often as I could without raising suspicion from my Mother. Then I had a better idea. I told my Mother that it was time for me to move out. I was in college part time, and I did have a job in an office.
She said that I didn’t make enough money to afford my own place. I agreed, and I told her that I was going to move in with Earl. He had an extra bedroom, and we had agreed to share the rent.
Mother thought it was an excellent plan. She said, “You two get along so great. I don’t know of any other Brother and Sister who are so close.” If she knew how close we really were, she would drop dead of a heart attack.
So now we live together, and I am very happy. I think Earl is too. When one of us gets home before the other, we wait completely naked. One evening when I came in to find Earl sitting in his chair, with his stiff cock up in the air, I had a little fun.
Without a word, I took off all of my clothes, and just sat down on his cock. When I was all the way on down his lap, with his long cock buried in my ass, I turned to him and said, “Honey, I’m home!”
One weekend we spent Friday night through Monday morning with no clothes on. We were completely naked for the whole weekend. I lost count of how many times Earl fucked me that weekend. I walked around the apartment with cum oozing out of my asshole, and trickling down my leg.
He was exhausted on Monday morning. He could hardly get out of bed. I am surprised that he didn’t need a blood transfusion.
We do not use the lube any more. He has stretched my asshole out to just the right size, and he says he prefers a little resistance when he pushes in. It takes a little longer to get it all the way in, but it does feel good.
When I realized that he liked it that way because it reminds him of the days with Robert, I had an idea. I asked him to always call me Roberta, not Kitty, when we were alone in the apartment.
I think I am developing a new persona as Roberta for when we are alone. I even got my hair cut short, and the stylist called it a “Boy Cut.” My breasts are not large, but now I try to de-emphasize them even more. I have started to wear mens shirts and jeans around the apartment.
All of the men I know, including the men in the office, must think I am a lesbian. I clearly don’t have any interest in them, and my boyish look is obvious. What is funny is that I am not a masculine looking woman who likes to have sex with other women. No one would ever guess that I have taken on the look and personality of an effeminate guy who loves to be fucked in the ass.
Earl must feel like he has his Robert back, only now he is an adult who has been transformed by surgery into a woman. That is, a transsexual person who has a simulated vagina but does not use it. I love to have my clit licked to give me an orgasm, but I have no desire to take Earl’s cock up that hole.
I don’t know if I would have turned out to be so anally erotic if I had not been introduced to sex the way I was. My sexual preferences were fused in my personality by watching my Brother fuck his boyfriend in the ass.
I am happy to have my Brother’s cock in my ass several times a week, and I don’t think he misses Robert any more.
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