I was 21 at the time and in college. My GF and I had gotten handsy and made each other cum plenty of times, but always with clothes in the way, so I’d never touched her pussy directly before (boobs we’re another matter - I couldn’t get enough of touching them, nor could she!). One night her roommate was gone so I slept over in her dorm. This seemed like a perfect opportunity.

We were making out in our pajamas and her shirt had come off. My hands eventually left her nipples and strayed south. After some gentle touches between her legs that made her gasp, I decided to give it a try. I slipped my hand just inside the waist band of her pajamas and discovered she wasn’t wearing underwear (unusual for her at that point). “Is this ok?”, I asked, expecting her to say no. She just nodded.

I moved my hand down and felt the warmth and incredible wetness of her pussy lips. She gasped. I rubbed gently, doing what I’d learned she liked from outside her clothes. Eventually my middle finger worked its way to her pussy opening and I started to insert it.

“Is this ok still?” I asked again. She gasped and nodded. I pushed in deeper. I’ll never forget the way her virgin pussy felt - soaking wet, warm, squeezing gently around my finger, and distinctively textured as my finger moved against the folds of skin inside toward what I’d later discover to be her G spot.

As I said, I’d made her cum plenty of times before this, but this time was by far the most intense. Afterwards, as I told her how much I enjoyed having my finger inside her, she confessed she wasn’t sure I’d be willing to do that but that she’d wanted it more than anything. Lucky for her, that night was the start of me doing just that as often as I possibly could.