Lilly the First

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.

We began our lovemaking as we always did, with deep kisses with busy tongues, with my hands and mouth all over her body. This time Lilly had unfettered access to my erection, and her words and actions advertised her nervousness. "Will it fit?" she whispered, and I assured her that it would, as I'd been able to get two and sometimes three fingers into her aroused vagina.

If truth be told, we were both nervous. My fingers and my tongue got her body ready, and then... it was time to take the next step. Just as we would do in the car, Lilly lay on her back and opened her legs for me as I mounted her, hovering my body above hers and probing my cock against her silky wetness. Though for the first time, neither of us had clothes blocking our skin-to-skin contact.

It was initially awkward, of course. Our faux intercourse "dry humping" had familiarized us with how Lilly's legs had to open and how I had to perch myself above her, supporting my weight with my elbows and knees, and how to get my erection into the general vicinity of her vagina. It was a learning experience, albeit a short one, to understand how Lilly needed to raise her knees a bit higher and to adjust her hips to present her inflamed vulva to me, and how I needed to adjust my hips and, with a hand reaching down to aim my shaft, how to position my cockhead at her opening.

And then... I nudged my hips forward and sunk in and discovered heaven. Feeling Lilly's vagina with my mere fingers was far, far less sensual than feeling it with my penis, or what my penis feels when I masturbated. The sensations of a real vagina are intensely erotic and arousing, with an incomparable soft embrace of slickness and warmth, together with the psychological awareness that *my* intimate body part was inside *her* intimate body part as I watched her face and listened to her breathing and her noises and her excitement as I was penetrating her, stroking her and burying myself inside her and sliding in and out, in and out.

Lilly had long-since lost her hymen, if she ever had one in the first place. I slipped into her easily because she was juicy and my precum was adding to that slickness. "Oh oh oh" came from her open mouth. "Are you all the way in?" she asked, and I pressed my pubic bone hard against hers to show her. Gasps and moans from both of us, an occasional "Oh god" and "You feel so good".

How long did I last that first time? I don't remember, though I doubt it was more than a few brief minutes. The intensity and the newness of the sensations was simply too much for me to have more control. I do remember saying to her, "I'm going to come" and her telling me that it was okay, and then I gave up any pretense of trying to be a studly, experienced lover and just began my final strokes, full-length and powered by my strong legs.

I surrendered to Lilly's sweet embrace and exploded, my body almost paralyzed with clenched muscles and overwhelming pleasure. I pulsed my liquid heat, again and again, and my mind's eye recalled visual memories of my ejaculations when I masturbated, as I was now filling the deepest recess of her vagina with those same flying spurts.

Afterwards, I do remember being reluctant to withdraw, as I have always been since that first time. My erection softened and I slipped out, and I slid beside Lilly on that narrow bed and continued to embrace her and to caress her body. "I felt you," she told me.

"What did you feel?"

"I felt you get stiffer. Then it kind of jerked or throbbed or something like that. And then I felt myself get wetter. A lot wetter."

A few minutes later, I could see my white fluid oozing from her vagina. I remember feeling how raw and primal that was, that my lover had accepted my erection inside her body and accepted my ejaculations, my semen, which created our joint "soup". We rested together, kissing and whispering and touching, and before too long my erection returned. I mounted Lilly again – this time less awkwardly – and I slid inside her silken walls with their noticeably increased lubrication.

I lasted longer, though the physical and emotional sensations were almost as intense as the first time. We experimented with different movements, different rhythms, and different positions. When my arousal rose toward my climax, I'd withdraw and we'd shift from me on top to her on top, to her lying on her front and me entering her from behind, to her on top again until her knees got too sore. And in the end, as before, we returned to the missionary position with Lilly's knees held high by my thighs and me continuing to try to help her reach that elusive orgasm before my own shuddering, powerful climax brought an end to my erection.

"Do you want me to keep touching you? Down there?" I asked, as I would always do, and Lilly would always say no, as she was too sensitive, that she didn't think she could come. Our sleep was short and restless, as the narrowness of the bed was uncomfortable and I needed to get her out of the dorm before 6am and over to her friend's womens' dorm across campus. We made love one more time in the early morning hours, beginning with my mouth on her musky pussy and ending with yet another "I'm getting close" from me and Lilly's "Do it do it" response and the liquid pulsing of my fluids into her vagina.

We rendezvoused later that morning at a campus coffee shop after we both had showered and cleaned ourselves up. We had two hours before Lilly's bus would take her home. "So I guess we finally did it," she said as she stirred cream into her coffee. "I'm not a virgin anymore."

"Neither am I. You were my first, too. Are you okay with it?"

"Yes. I've wanted to do that for a long time."

My mind drifted to the previous evening and the early morning before dawn. "There's a big wet spot on my sheets from last night. But this morning, we left my room before... you know, before much leaked out."

"It went into my panties when we walked. After I showered, I put on fresh panties." She looked down at her coffee. "It's still leaking a bit."

"Is that going to be a problem when you get home?"

"I'll wash my underwear by hand. My mother won't see it, if that's what you mean."

"What does that feel like? The leaking?"

Lilly looked at me and smiled. "I like it, actually. It reminds me of how it got inside me." From that moment on, I was hooked. Hooked on Lilly, hooked on real sex, hooked on bareback fucking.

I didn't see Lilly again until Christmas Break, and then we went for a long date and drove the 50 miles back to the University and back. There, once again in my dorm room, we fucked, though this time we were probably the only students who were in the building. Lilly allowed herself to be delightfully noisier. She visited the University again in the Spring, though this time we managed just one round of lovemaking before we got busted by the Resident Advisor and I had to deliver Lilly to her friend from high school.

That Summer after my freshman year was bittersweet, as Lilly had gotten accepted for the Fall semester at a prestigious all-women college in the East. We fucked a couple of times in my mother's Corvair, which was even more uncomfortable than my dorm room twin bed, though far better than our previous "dry humping". You take what you can get, right?

I flew East to see Lilly in the late Winter as her date for a big dance. I stayed two nights in a bed & breakfast near her campus, and she sneaked in both nights to sleep with me in a queen-size bed. Oh, and we made love those nights, too, though there we had to be quiet and not get caught by the woman who ran the B&B and felt protective of the college's female students' virtue. On the third night I booked the smallest and cheapest room at a large downtown high-rise hotel – again, with an uncomfortable twin-size bed bed – and as I recall we fucked three times. The guy who delivered the room-service breakfast seemed amused.

And that was the last time Lilly and I ever had sex together. She and I both lost interest in a long-distance relationship. The next summer I got a job in the East and Lilly went home, and we both found other relationships. We continued to see each other, off and on over the years, albeit platonically. We were, after all, each other's First, and that will always be the case in our hearts.