A couple years back we hosted our extended family over for Christmas. My sister walked in on me masturbating in my bedroom (I have a pretty major addiction, and get off multiple times a day regardless of circumstance), she was 22 at the time. I panicked immediately, but instead of freaking out, she giggled and stayed, closing the door behind her. I didn’t know what to think, so I just stood there frozen with my hand on my dick. She looked at me for a second, and then said “Well go on!”
I hesitated, not really believing what the fuck was going on, and she sighed, seeming almost annoyed and then walked over to me. “like this?”, she said as if coaching me, as she reached down and moved my hand up and down along my cock. I blushed beet red, and then slowly started doing as instructed. I held her gaze, unsure of what to think, but she just looked back at me with this amused twinkle in her eye, and I started to get really turned on. As I got me into, she seemed pleased, and came close to me again and started jerking me with her own hands. She surprised me with her skill as she played with my balls with one hand while stroking me with the other.
It didn’t take long for me to come close to finishing, and she quickly pulled down the front of her panties and wrapped her pussy over the top of my cock and started rubbing herself back and forth on my dick. I came almost immediately, and she held my cock between her legs as I came, filling her panties with my cum. Once I finished, she giggled, pulled up her panties now full of my cum, and pecked me on the cheek, then turned to leave. As she stepped out the door she said “oh btw, dinner is ready!”, then scooted out the door and went back downstairs with the rest of our family. I still have a difficult time processing wtf happened, but holy fuck did I find it hot. Neither of us have ever spoken about it since, but I secretly hope every year that she’ll walk in on me again for the same little surprise.
Feel free to hmu if you wanna chat about this at all!
Source: reddit.com/r/gonewildstories/comments/i2fty9/my_22f_yr_old_sister_jerked_me_off_into_her