38 now, 27 then
When I was 27 I was cruising a local phone chat line and started to talk with a 19 year old girl named Tracy. Within the hour of my free trial membership I had learned she was 19, blonde, bi, 5'3' and had just graduated high school.
We made a date, the first of which was a basic meet and greet, bite to eat and quick kiss.
Our second date was filled with nothing but sexual tension. We found an excuse to go back to my place, where we kissed and fondled until we were both naked.
Tracey and I lay back on opposite sides of the couch and without saying a word we both started masturbating. She had two fingers in her blonde bush and was playing with her DD breasts while I pumped my seven inches and rubbed precum all over the head.
Without saying a word I wet the middle finger of my left hand with my natural lube, reached out and slid it into her asshole. She never tried to stop me, she just kept jilling until she came over her hand.
After she had caught her breath, Tracy replaced my hands on my cock with her own and stroked me off to a huge load all over her tits.
She lay there, rubbing my cum into her tits, looked up at me with a smile and said, 'Now do you wanna see what my mouth can do?'