When I was a senior in high school I was dating this girl who was really shy about any sexual activity. This was, in person, at least. She’d actually instigate that we’d trade nudes almost nightly, but whenever I wanted to do something physical she’d nervously turn it down.
One day I was over at her house with her mom. My girlfriend was in her bedroom doing homework while I watched a movie with her mom in the living room. My girlfriend was doing some math homework she found difficult so I offered to go help. Her mom was hesitant at first because she wanted her daughter to not “be given the answers”, but eventually she gave in because she was getting sleepy on her couch. The one condition was the door had to be kept open.
I was a big liar about the whole thing, however. I did know how to do math, but that wasn’t what I was there for. My girlfriend watched as I walked into her room and climbed on the bed. I reached into my pants and pulled my already hard cock out right there. She panicked, her eyes grew wide, and moved her hand forward to gesture me to put it away. I’m guessing she was more alarmed because she didn’t know her mom was half asleep. Instinctively, I grabbed the hand she inched forward and wrapped her palm around my cock.