Lilly and I met at church. We were both seniors at different high schools. She was smart and funny, a few inches shorter than me with short, dark brown hair and a trim athletic body. We fell for each other quickly.
And we were both virgins, despite being 18. This was back in the Old Days when (at least among our peers) the vast majority of high schoolers were virgins. Condoms were kept behind the pharmacist's counter and only handed out with a stern gaze from the pharmacist to an embarrassed customer, and the Pill was in its early years. For most of us, we looked ahead to our college years to reach our sexual adulthood.
That's not to say that we didn't fool around in high school. Lilly and I kissed on our first date and had a heavy makeout session on our second. I had my hands on her clothes-covered breasts on the third date and bare breasts on the fourth. On our sixth date we parked at 9pm midwinter on a Friday night in the empty church parking lot in my mother's Corvair. For those unfamiliar with that model, one big benefit was bench seats, not bucket seats. Lilly and I embraced and half-reclined in the front seat, and there Lilly allowed me to progress to getting a hand beneath her skirt and down her panties.
Lilly was shy, though very much happy to have my fingers caressing her swollen labia and stiff clitoris and occasionally dip into the wonder of her vagina, as I enjoyed feeling her vulva opening wider and wider and flowing with her juices. She would gasp and moan in my mouth as we continued to kiss. Alas, my inexperienced fingers and her inexperienced awareness of her own body (as she confessed that she never masturbated) were not able to bring her to an orgasm.
Things continued like that for the rest of the winter. By early spring we were regulars in a suburban subdivision that was under construction, dark with no streetlights and populated at night only by the occasional car containing other lovebirds. We were in a pattern of kissing, then fondling, then getting horizontal. Lilly would lay on her back and I would mount her, both of us fully clothed, and we would "dry hump" until I climaxed and made a mess in my underwear.
And sometimes when I brought Lilly back home, we'd sit on her living room couch and chat until her parents went upstairs to bed, and on several occasions we were bold enough to have Lilly lay on her back while my face was between her legs, her skirt draped over the back of my head and her panties clutched tightly in her fist. With Lilly I learned how much I enjoyed cunnilingus, which was far superior to just fingering her, as now I could taste and smell and lick her pretty little pink (and swollen and slick) parts.
Unfortunately, I could never bring Lilly to a climax. Her arousal would climb, her breathing would accelerate to gasps and throaty grunts and moans, and then she'd remain stuck at a plateau and never find her release. Looking back, it was a combination of both my inexperience and hers, and no doubt compounded by our constant fear of being caught by a roaming police car when we were parking, or by her parents supposedly tucked away upstairs in their bedroom or her younger sister in her bedroom.
Moreover, our circumstances were never conducive to our "going all the way." Our primary concern was a fear of pregnancy, and we made sure that the end result of our "dry humping" never came near to her bare pussy. Winter became Spring, and after graduation, Lilly's mother took Lilly and her sister to an out-of-state lakeside cabin for most of the summer with their cousins. As much as Lilly's parents liked me, it became apparent to both of us that her parents were becoming increasingly (and rightfully) concerned that our makeout sessions would inevitably transition to full-on sex. Her parents were happy to separate Lilly and me for a couple of months.
In late August I began at the University that was 50 miles from home, and Lilly continued to live at home, work, and take classes at a community college. It was a frustrating continuation of our enforced separation. The saving grace, however, was that in the Fall, Lilly's mom took Lilly to the doctor to get a prescription for birth control pills. Ostensibly her mother's stated reason was to "regulate her period", though to both Lilly and me that included the useful benefit of ensuring that even if-and-when Lilly (and I, or with some other guy) made that transition to having intercourse, that Lilly would safely continue to have her periods.
Of course, putting Lilly on the Pill was a tacit acknowledgment that if we weren't having intercourse because we (and her parents) feared her getting pregnant, then eliminating that fear would almost certainly result in us having intercourse. The inevitable occurred later that Fall when Lilly made arrangements to visit a former high school classmate at my University. Lilly told her parents that she was spending Saturday night with the classmate in a womens' dorm, although the reality was that she would spend the night in my dorm room – and in my bed. And we would finally "do it" for the first time.
When the fateful weekend arrived, my roommate was himself back home visiting his parents, and it required only a moderate effort to sneak Lilly through the back door of my gender-segregated mens' dorm and up the stairs to my room. And there, finally, we were able to get naked together. I had only a twin-size bed, but passion trumps discomfort.
Lilly and I experienced a number of "firsts" that night. It was the first time we'd seen each other's naked body. I'd been touching her bare breasts and pussy for the past nine months, and I'd been going down on her for the past four months, though this was the first time Lilly had her hands on my bare skin in an intimate way.
