[M]y 22[F] yr old sister jerked me off into her panties at a family Christmas party

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.

[M]y 22 yr old sister [F] drank a shot of my cum unknowingly at a party in college

We both went to the same college at the time. I was at a residence party one night, and the host thought it would be funny to leave shot glasses in the bathroom for any brave guys to cum in and make ‘cum shots’. They had a little wager going that if someone actually filled one, they’d offer $100 to any girl that would shoot them (however many were filled by midnight).

Anyway I got pretty drunk, and during one quick leak break, I drunkenly decided to go for it. They were mismatched glasses, and being the hilarious comedian I am, I nutted into the one with the weed leaf on it. I finished up, and left the bathroom. By the end of the night, 2 other guys had followed my lead, so there was a total of 3 cum shots up for grabs. At midnight our host offered up his reward for any takers, and I just about died when my sister (who I had no idea was there) jumped forward, clearly drunk, with her hand raised high. I was too embarrassed to say anything and reveal I was one of the 3 who donated to the cause, and I watched as she downed the first 2 shots, both of the other guys glasses. I had a weird feeling of disgust but also extreme arousal watching this happen, and my heart started racing as she reached for my glass. I wanted to look away, but couldn’t stop staring as she put the glass to her lips and shot my cum down her throat. She spilt a little down her chin but caught it with her thumb on her chin just as she coincidentally made eye contact with me across the crowd. Her cheeks flashed crimson red as she saw me and quickly cleaned off her chin before slipping away to claim her reward from the host.