I got a late start on losing my virginity, which was pretty much the norm growing up in my moderately conservative suburbia in the mid Sixties. In my last year and a half of high school I dated Leanne. We were the same age, though she was a year behind me at a different school because her parents had held her back for a year. I met her at a friend's party, and we hit it off.
Leanne and I dated regularly. Being teenagers, our mutual attraction and our hormones had our make-out sessions get progressively more intimate. By late in my senior year, when we were both 18, we ended most of our dates at a secluded parking spot, both of us horizontal and fully clothed in the back seat of my mother's car. Our busy mouths would lock in nonstop wet kisses while my hands reached inside her blouse to fondle her breasts. Eventually we'd slip into the missionary position, and I'd rub my erection against her crotch, separated from her pussy by three layers of cloth, until I climaxed.
Sometimes we'd skip the parking spot and instead end a date at her home. After her siblings and parents went upstairs to bed, we'd make out on her living room couch. If we felt bold enough and horny enough, Leanne would lie back on the cushions, my head would maneuver under her skirt and between her thighs, and she'd pull her underwear aside to allow me to lick and suckle her sweetness for a few minutes. Alas, she never climaxed, which was understandable given her anxiety about her parents and siblings upstairs in their bedrooms. Still, those experiences cemented my love of cunnilingus in all its glory of scent, taste, and intimacy.
Leanne and I never 'went all the way' during my high school years because of a fear of pregnancy. Early in my first year at the University, which was an hour away from home, things changed. Leanne phoned to tell me that her mother had taken her to the doctor to get her on the Pill. "She thought it was a good idea to 'regulate my period'," Leanne whispered, "We can 'do it' now, right?" Her mother was no dummy. The truth was more likely that her mother concluded that her daughter's virginity wasn't going to last much longer, and that reliable contraception was better than a teen pregnancy.
Leanne visited my campus a month later for a weekend, ostensibly to spend Saturday night with a first-year girlfriend in a womens' dorm who Leanne had known from high school. In reality Leanne spent the night in my dorm room. We didn't get much sleep. For the first time we were able to get naked together, and nature took its course.
Leanne had no hymen and no discomfort, and our lovemaking was both romantic and passionate. We began with our usual cuddling and kissing, albeit this time with both of us naked, and continued on to the same glorious licking of her pussy. This time things didn't end there. Eventually I mounted her and slid my sensitive, steel-hard shaft deep inside her soft, warm, slippery silkiness that I'd previously only explored with my fingers and tongue. The exquisite sensations were a revelation, and from that day onward I was addicted to bare skin to skin intercourse, to both the physical and emotional pleasures of it, and most especially addicted to the explosion of pleasure when I unleashed my ejaculations inside a vagina.
To our mutual regret, just as it had been earlier when I was only able to go down on Leanne, and despite my best novice efforts with my fingers, mouth, and cock, she still wasn't able to climax, though I certainly did. Three times that first night. "I feel you leaking out of me," she told me at early the next morning after we snuck out of the dorm and walked to a nearby coffee shop.
Leanne and I had moved to a new stage in our relationship. We did our best to get together throughout the remainder of the school year. At winter break one of our "dates" consisted of us driving from home back to my almost deserted campus, and there we got naked and juicy in my dorm room. On one visit home in early Spring, we returned to our parking spot and managed a quickie in the back seat, this time with her skirt pulled up above her waist and her underwear pulled down around one ankle, thrusting my cock deep into her snug, wet velvet until I blasted my hot streams.
Over the summer months between my first and second year, I lived at home and worked at a fulltime job, and Leanne and I found only a handful of opportunities with sufficient privacy to do the deed. Sadly, things came to an end in August, just before I headed back to the University and Leanne would soon depart 1,000 miles east to attend college. We agreed that a long-distance relationship wasn't going to work. It was time for both of us to date other people.
And so I began my second year with fond memories of Leanne -- her spirited personality and, yes, her body, and how much I enjoyed foreplay and intercourse. Now I was on the lookout for who might come next into my life. I had moved out of the dorm and into a 4-person 2-bedroom apartment with three friends I'd met at the first year dorm. Sharing an apartment bedroom wasn't much different than sharing a dorm room in terms of having to negotiate with your roommate for private time, though it still held the promise of being more convenient than the dorm for entertaining members of the opposite sex.
I ran into Charlotte while we were both waiting in line to sign up for the Fall semester classes. She was a familiar face from my high school, though back then we were just friends and never dated. As second year students, we were both unattached and just seemed to gravitate together. Charlotte was shorter than Leanne -- about 5'2 -- and carried just a bit of lingering Freshman Fifteen. She had long, thick, brown hair that descended to her lower back, and she combined that with twinkling blue eyes, a steady smile, curvy hips, and breasts that were bigger than baseballs and smaller than softballs.
We began to see a lot of each other. Charlotte lived in a dorm in another section of the larger campus, and I would escort her home riding together on the University shuttle bus. Before long we were making out on the fifteen minute bus ride, and that soon evolved to making out on my apartment couch. The first time my hand wandered to cup a breast, Charlotte grabbed my wrist. "No, don't. I can't."
"Okay. I'm sorry."
"It's just..." she paused. "My mother told me I should be a virgin on my wedding night."
"Okay," I told her, kissing her neck. "I was only trying to be affectionate."
"I just need you to know," Charlotte managed to murmur before she groaned and squirmed from what my mouth was doing to her neck, and we slipped lower onto the couch and resumed our embraces and nuzzling kisses.
Okay, yes, I was nineteen and male and horny. After that I didn't aggressively paw Charlotte. I tried to avoid being obnoxious about where my hands might wander. I did, however, occasionally test her boundaries during our frequent steamy, mutually breathy and heart pounding encounters. My patient seduction across the next several weeks was rewarded by Charlotte's gradual, ever so gradual surrenders.
