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My Family
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Straight Male / 38
I Slept With My Sister
I started having sex with my sister when I was 13 and she was 14. She started giving me signals when she was 13, but I was too naive to notice them back then. She would do stuff like wear baggy lowcut shirts to bed and bend down in front of me so that I could look down her shirt.
The actual physical contact didn't start until a few months later. We had mutual friends, Chris and Megan, that we're obviously into each other. We joked about it constantly. One day she was pretending to be Megan, and she shouted "Oh, Chris" before she started making kissy sounds and kissing me all over. I pretended to be Chris and reciprocated. As we were doing this, we would occasionally "miss" and kiss each other on the lips. She pretended that it was an accident, but it's obvious that she was doing it on purpose in retrospect.
Over the next couple of weeks, we did this pretend game a few more times before I just kind of lost it. In the middle of her pretending to be Megan, I just reached out and grabbed her breasts. She stopped for a second before saying, "You know I'm still your sister, right?" As soon as she said that, I looked down in shame without saying anything. After a brief pause, she finally added, "...But Megan isn't." As soon as she said that, I looked up at her, and we just started making out. She kissed me with an open mouth while we dry humped and felt each other up.
After that, we would hookup anytime we were home alone. We went through these cycles where I would try and take things further and she would push back before relenting a few days later. I remember slipping my hand under her shirt the first time. She instantly pulled my hand away, but a couple of days later she took my hand and placed it under her shirt when she wasn't wearing a bra. The same thing happened a few weeks later when I tried to slip my hand down her pants. She initially pulled my hand away, but a few days after that she grabbed my hand and thrust it into her pants so that I could slip my fingers into her.
Eventually, we got to the point where she would either ride on my naked cock while she wore panties or she would grind her naked pussy over my boxers. She was very freaked out over the idea of getting pregnant, so genital contact was initially off the table. My older brother had a stash of condoms, and every time I suggested we grab one, she made it clear that she didn't want to have sex. She did eventually start giving me hand jobs and blow jobs, though.
Around the time she turned 14, she went on the pill for unrelated medical reasons. I was hoping she would be open to sex, but she was still worried about getting pregnant. A few months later, we were hooking up, and it was getting intense. She was grinding up against me, and it was obvious that she was into it. I came prepared that time. I had grabbed a condom from my brother's stash before we started making out and put it in my pocket. As soon as things got intense, I pulled the condom out, showed it to her, and nervously whispered, "Do you want to?" She didn't really say anything. She just laid down on her bed and looked up at me. I think she figured that we would be safe since she was on the pill in addition to me using a condom.
I pulled my boxers down and slipped the condom on, but I had no idea what I was doing. I tried to just ram my cock into her, and she winced in pain before pulling back. I tried again, but she put a stop to it before I had a chance to get inside her.
A few weeks later, we tried again. It still seemed like she was in pain, but at least this time I managed to get inside her. Since it was my first time, I came after only a few seconds. We tried several more times over the next few weeks, and eventually it seemed like she was starting to enjoy it. Over the next few months, we would just have casual sex with each other whenever we could. I would usually go into her room, we'd fuck, and then we'd just hang out for a while before I went downstairs to our basement to watch TV.
The most amazing experience I had with her was in the summer, a few months after we started having sex. I was sitting on the couch downstairs watching TV with her before our parents left to run some errands. As soon as we heard the door shut, she was on top of me, and we were making out. I very clearly remember she was wearing a blue sun dress with little white polka dots. As soon as we got the point where I was about to run upstairs and grab a condom, she just took her panties off and slowly lowered herself onto my bare cock. By then, we had sex enough times that the fear of getting pregnant went to the back of her mind. She mumbled, "I'm on the pill," and I just instantly came inside her. To this day, it is the best sexual experience I have ever had.
Shortly after she turned 15, she started dating, and that was the end of us hooking up. I still see her all the time, but we never talk about what we did. Today, we're married, but I would absolutely fuck her again if she let me.
The actual physical contact didn't start until a few months later. We had mutual friends, Chris and Megan, that we're obviously into each other. We joked about it constantly. One day she was pretending to be Megan, and she shouted "Oh, Chris" before she started making kissy sounds and kissing me all over. I pretended to be Chris and reciprocated. As we were doing this, we would occasionally "miss" and kiss each other on the lips. She pretended that it was an accident, but it's obvious that she was doing it on purpose in retrospect.
Over the next couple of weeks, we did this pretend game a few more times before I just kind of lost it. In the middle of her pretending to be Megan, I just reached out and grabbed her breasts. She stopped for a second before saying, "You know I'm still your sister, right?" As soon as she said that, I looked down in shame without saying anything. After a brief pause, she finally added, "...But Megan isn't." As soon as she said that, I looked up at her, and we just started making out. She kissed me with an open mouth while we dry humped and felt each other up.
After that, we would hookup anytime we were home alone. We went through these cycles where I would try and take things further and she would push back before relenting a few days later. I remember slipping my hand under her shirt the first time. She instantly pulled my hand away, but a couple of days later she took my hand and placed it under her shirt when she wasn't wearing a bra. The same thing happened a few weeks later when I tried to slip my hand down her pants. She initially pulled my hand away, but a few days after that she grabbed my hand and thrust it into her pants so that I could slip my fingers into her.
Eventually, we got to the point where she would either ride on my naked cock while she wore panties or she would grind her naked pussy over my boxers. She was very freaked out over the idea of getting pregnant, so genital contact was initially off the table. My older brother had a stash of condoms, and every time I suggested we grab one, she made it clear that she didn't want to have sex. She did eventually start giving me hand jobs and blow jobs, though.
Around the time she turned 14, she went on the pill for unrelated medical reasons. I was hoping she would be open to sex, but she was still worried about getting pregnant. A few months later, we were hooking up, and it was getting intense. She was grinding up against me, and it was obvious that she was into it. I came prepared that time. I had grabbed a condom from my brother's stash before we started making out and put it in my pocket. As soon as things got intense, I pulled the condom out, showed it to her, and nervously whispered, "Do you want to?" She didn't really say anything. She just laid down on her bed and looked up at me. I think she figured that we would be safe since she was on the pill in addition to me using a condom.
I pulled my boxers down and slipped the condom on, but I had no idea what I was doing. I tried to just ram my cock into her, and she winced in pain before pulling back. I tried again, but she put a stop to it before I had a chance to get inside her.
A few weeks later, we tried again. It still seemed like she was in pain, but at least this time I managed to get inside her. Since it was my first time, I came after only a few seconds. We tried several more times over the next few weeks, and eventually it seemed like she was starting to enjoy it. Over the next few months, we would just have casual sex with each other whenever we could. I would usually go into her room, we'd fuck, and then we'd just hang out for a while before I went downstairs to our basement to watch TV.
The most amazing experience I had with her was in the summer, a few months after we started having sex. I was sitting on the couch downstairs watching TV with her before our parents left to run some errands. As soon as we heard the door shut, she was on top of me, and we were making out. I very clearly remember she was wearing a blue sun dress with little white polka dots. As soon as we got the point where I was about to run upstairs and grab a condom, she just took her panties off and slowly lowered herself onto my bare cock. By then, we had sex enough times that the fear of getting pregnant went to the back of her mind. She mumbled, "I'm on the pill," and I just instantly came inside her. To this day, it is the best sexual experience I have ever had.
Shortly after she turned 15, she started dating, and that was the end of us hooking up. I still see her all the time, but we never talk about what we did. Today, we're married, but I would absolutely fuck her again if she let me.
- That's Juicy! 80
- Remove It! 8
