When I was a freshman in college in the dorms I would walk from my room, in my standard basketball shorts and tshirt down to the front desk where a chick manned the desk on some days of the week, she was a fourth year and had a pin up style look to her, totally sexy brunette. I crushed on her hard and decided I'd start going commando to pick up my mail from her every week... One day I caught her staring at me, down there, and I got so excited my face turned red and I was so overwhelmed I had to make up an excuse and get out of there (I was 18 and was just coming into my confidence)
I flirted with her on and off for a while and ended up at her room one late night and I made my move. We made out passionately for a while and then she cautiously asked me if she could touch it... She was shy, very shy. So her asking me to touch it was a big deal for her I think. She definitely felt naughty asking me to simply touch it.
She ended up giving me the most gentle hand job of my life, very different than what I was used to. It must have taken me 45 minutes to finish, but I didn't mind at all. Half way though I asked her if she wouldn't mind using her mouth, and she said "not tonight, next time..." So The last night of our time in the dorms came and I had been up for about two days straight on a weekend road trip, so as soon as I got back to the dorm that night, I completely passed out... I woke up the next morning from a Text from her asking if I could come over that night to take her up on her offer before we all went home for the summer...
By the time I saw the message the next day she was already half way across the state on her way home...