Several years ago, during a period of life where I was between wives, I ended up dating a gal who at the time was a 36 year old virgin. Before we even had our first date she'd told me that she was a virgin, and planned to stay that way until she was married. She also wanted to have several kids which I thought was unrealistic at her age, and which ultimately led to my breaking up with her after 10 months.
I had known her for a few weeks before we actually went out on a date, and during that predating time she clearly let me know that she was interested. Our first couple dates were the usual getting to know you questions and answers, but by the third date she was freely allowing my hands access underneath her clothing and to my surprise she started to rub my cock through my jeans.
I didn't need a lot of encouragement and on our next date I unbuttoned and unzipped my jeans and she easily slid her hand inside my pants. She later told me that she'd given hand jobs to a couple of previous boyfriends but that was as much as she'd ever done.
A couple of weeks later I finally managed to get her clothes completely off and she asked me "what do we do now, I've never been naked before with a man?" I offered that we didn't have to do anything different, but after an hour on the couch she suggested going to the bedroom.
This quickly led to a ritual of my trying to see how fast I could get her clothes off, and then moving into the bedroom where she would proceed to play with my cock and eventually jack me off.
She insisted that she loved to see my cock squirt and would usually lay her head on my stomach and watch me cum. This position offered her a close up view as she explored male anatomy up close for the first time. It also often provided her a squirt or 2 of cum on the face which she seemed to enjoy and was in no hurry to wipe away.
It wasn't long before I decided it was time to give her a real close up view of me cumming so after arranging her on the bed, and as I straddled her chest, I told her to keep on playing with me and jack me off straight unto her face. All of this was new to her, but she was always willing to try something as long as sex wasn't involved.