Rebecca and I started seeing each other in the summer of 11th grade. I had been with two other partners, she hadn’t been with anyone before. We spent the summer hanging out nearly every day. Making out, then making out with her top off, eventually her going down on me, me going down on her, she just wasn’t ready for sex.
When we were starting back up 12th grade, we were hanging out at her parents place one night after they had all gone to bed. We were making out, her in this sexy dress she had, no underwear on… I picked her up and was grinding my cock against her pussy. We were both so wet and aroused, I had been playing with her ass a bit before and my cock slid in, she moaned loudly, and sunk herself deeper on my cock, before realizing what was happening. She sat there for a moment before sliding off me.
We kept making out and she said she still wasn’t ready. Fast forward a year, on her 18th birthday we had sex, and soon after had gotten right into anal.