Fooling Around With My Best Friend's Sister

When I was barely a teenager my best friend Ryan and I were mostly inseparable. Eventually I got old enough that I was able to have sleepovers with him, and as long as my homework was done my parents let me stay over with him really as often as I wanted because his parents could easily take me to school with him. His family kind of became a second family to me as often as I was there. Eventually they bought this super comfortable cot for me that I would unfold and it fit in this little nook in his room perfectly. It probably wasn't actually that comfortable but I thought I was so cool having a bet at my best friend's house. After a while I even had my own drawer of clothes in his dresser. I just want to get it across that I more or less lived there as much as I lived at home.

There was a period of about three months that I couldn't stay with him though. A lot of stuff around the end of year holidays, his family traveling and mine being busy, we just didn't have time to. So after the new year but before school started back, I went over to stay with him again. He had just gotten an NES for Christmas so we played it nonstop. His younger sister Lucy hung out for a while then went to her room and eventually we decided to call it a night too. But about five minutes after the light was out his door opened slowly and Lucy walked in, and all she said was "can I do it?" Ryan shot up out of bed and pushed her out into the hall and I heard him say kind of gruffly "no he's still here on the cot." He closed the door and got back in bed but of course I had to know what that was about, so I asked him what she wanted to do. He kind of awkwardly said she likes to play games at weird times and just rolled over. I let it go but knew something was up and was determined to figure it out.

The next day, Ryan's parents left for work and we ate cereal out of the box and drank a ton of soda and played video games for hours. They left us in charge of Lucy, which wasn't a big deal cause she stayed in her room most of the time anyways except to watch us play games. Ryan decided to take a shower at one point and handed his controller to Lucy, leaving her and I alone playing the NES. I decided this was the best opportunity and just asked her what it was she wanted to do when she came into his room last night. She got really embarrassed and said that he'd be mad if she told me, so I told her I wouldn't let him know so she just spilled it. I was shocked by what she told me, which was that she'd been going into his room every night and "sucking on his thingy." I asked if she meant his dick and she said yes. So I just found out that my best friend had been getting blowjobs from his own sister in the time I hadn't been around. I asked if she liked doing it and she said "a lot." Went on to find out that he would usually either finger her or eat her out during or after, and she loved that a lot. I told her I wouldn't tell him but wasn't really sure what to do with this information. Neither of us had ever had a girlfriend, I didn't think he'd even kissed a girl yet and I definitely hadn't so it was crazier to me to learn he'd been doing stuff than it was to learn it was with Lucy. My tiny brain at the time couldn't really grasp how fucked up that was.

The rest of the day goes by and I sleep over again. Lucy never came into the room that night but I laid there for a long time thinking about what it would be like if she did it to me too. The next day I was alone with Lucy for a while cause Ryan wanted some snacks with the money his parents left him and he rode his bike to the store, Lucy didn't go so I quickly volunteered to watch her so I could be alone with her again and after a few minutes I asked her if she'd do it to me too. I was surprised but she immediately said yes but was worried he'd come home and catch us. I formulated a plan for us to do it in the bathroom down the hall and if he came home she would just quickly walk to her room and I'd stay in the bathroom.

Well the good news was that he didn't come home too soon. I didn't know a lot about sex other than what I saw in my dad's porn magazines and the god awful shit that kids say to each other to sound impressive in school, but I did know what a blowjob was and that day I got my first one. We never even kissed, she just pulled my sweatpants down and started sucking. I came really fast and back then I didn't think anything about it but she swallowed all of it. She seemed so happy that it made me feel good and I asked if she wanted me to lick her, but she said no she was nervous he'd be home soon. We went back to playing NES and that was it.

There are plenty more stories that stemmed from that situation but I'm running out of room so I'll save another for later.