I was a yearbook and newspaper photographer in early high school, and my best friend's older sister--she was 19 or 20--asked me to take some pictures of her for her bf who was away in the Army. She did her make-up perfectly and put on a sexy fuzzy sweater, and we took some hot pictures with her wet lips and dewy eyes. I ran home and masturbated!! and thought of her a lot after that whenever I jacked off.
About a month later, she asked if I would take some more, and said it was kind of a secret, not to tell my friend. She drove me to her bf's apartmet, and when we got there, she took a nightie out of her bag, stripped down to bra and panties, and put it on. We took some provocative pictures, and she was very hot and flushed. I was shaking like a leaf! She took off the nightie and was there in her bra and panties, and then she unclasped her bra, let it drop, and held her breasts in her hands while I took more pictures.
She slipped her panties down over her butt for more pictures, and then took them off, but she didn't pose. She asked if I'd ever seen a girl's pussy before.
"No."
She kidded that I looked really hot and nervous. Her hand was between her legs now.
She asked if I ever jacked off, or she asked if I ever jacked off on her--I've never known which she said--and I had to admit that I did.
"I bet you want to now!"
"Yeah."
She told me to drop my pants. Later, when I remembered what happened, I realized she was masturbating all this time with her finger.
I slid my pants off and began masturbating, standing in front of her.
She watched, fingering herself, and encouraging me. I came pretty quickly, and then her eyes closed and she brought herself to orgasm.
Well, she told me NEVER to tell her brother about the pictures (he would have killed me), or her boyfriend that I jacked off (he also would have killed me). And I didn't!