Remembering When 2

Jeremy and I had been sleeping together for a month -- once or twice a week at his place, maybe once a week at mine -- before he finally asked me a familiar question that most new lovers eventually raise. We'd gotten each other all hot and juicy with a languid me-on-top 69, and when we couldn't stand it any longer, I just straddled him and gave myself a good scratching of my itches. My first orgasm was quick to arrive and peaked sharply, though it served more as a temporary tension reliever than an all-out climax. Jeremy just pushed up into me and held my hips and watched me ride it out, grinning at me with a bemused expression on his face.

I played with my second one, keeping it lurking right at the brink of no return, teasing myself to get suitably frantic. I squirmed on him and got us both quivering and panting and close. Too close, as I discovered, when in a sudden rush he thrust his hips high and squeezed my breasts and gasped, "Oh Annie, oh, oh, oh," and exploded his release within my tender grasp. He made amends by cheating his thumb against my clit until I surrendered with hyperventilating pants and appreciative grunts, a squirming pelvis and spasming cunt.

Afterwards, after we'd disengaged and repositioned into our nighttime spoon, Jeremy wrapped his arms around me from behind and fondled my breasts. "So," he began, "I've never asked you. How did you lose your virginity? Was it one of those horror stories with a pimply-faced kid with a hair trigger?"

I thought for a moment about how to answer. "That's a complicated question," I said simply. "It was the summer before college. He didn't have pimples. It was fine."

"What do you mean, 'complicated'?" Jeremy's tone was more curious than demanding.

"Not now," I demurred with a sleepy voice. "Maybe later. Long story." Jeremy's hand cupped each of my breasts in his goodnight ritual, seemingly uncertain which one would be the last he would touch. "I love you, baby," I whispered. I snuggled myself back deeper into his arms and drifted away.

- - - - - -

It was the summer after graduating from high school. Scott and I had been going together for six months. He was everything a teenaged girl could want: smart, cute, polite, and gentle. I'd had my share of boyfriends before Scott, one or two a year going back to eighth grade, and with each of them I'd learned more and more about puppy love and sex play. I'd had years of practice making out, and by my junior year I was fairly proficient at it. I felt comfortable enough with a couple of guys to allow them to touch my breasts, but nothing below the waist. That I reserved for my own fingers, masturbating almost nightly.

With Scott in my senior year I felt ready to take another step or two. I was sexually curious, even if I was a bit bashful, and Scott was the perfect unaggressive playmate who allowed me to take those steps whenever, and however far, I chose. That summer we both had fulltime jobs, though we were able to get together several nights a week for a movie, or a burger, or for quiet talks. Or for an hour or two of lip-locked passion in his mother's car, the Lovemobile.

We preferred his mother's old Chevy Impala to my mother's newer Thunderbird. Not that the Thunderbird wasn't fun to drive, but the back seat of the Impala was far more comfortable for times when the car stopped moving. Earlier that Spring we'd been rousted from one Lovers Lane or another. We'd only been making use of the front seat, both of us being both too shy and deathly afraid of being intertwined in the back seat when a police car made its slow, methodical pass and shone the high-intensity beam through our windows.

My stroke of genius was to suggest that we instead park in the huge local auto assembly plant employees' parking lot. The 3:30-to-midnight swing shift packed the parking lot with hundreds of cars and no people. We'd drive in, find an empty inconspicuous open spot, and know that as long as we kept our heads down, we'd be undisturbed for hours.

Of course, it was never a problem to keep our heads down, and it was even easier to do in the back seat without that pesky steering wheel getting in the way. We'd park, douse the lights, and dive into the back seat before the roving security patrol made one of its infrequent passes down our row of cars.

We were never in a rush. We'd finish our sodas and talk about our day, complain about our parents and our siblings, gossip about our friends. Eventually the conversation would dwindle and the unhurried necking would begin, with deep open-mouthed kisses and dancing tongues, pressed together bodies and squeezes and little muffled moans.

It was the classic progression that summer. When mere kisses became tame, Scott slipped a hand underneath my T-shirt to caress my bra-encased breasts and to discover my aroused nipples which were all too obviously delighted to be found. He soon learned to unclasp my bra with one hand, and I was eager for him to do it. After two evenings having my shirt and bra tangled up around my neck, I began to unsnap it myself as we drove into the parking lot and amuse Scott by extracting it out of my t-shirt sleeve before dropping it onto the floor. Once in the back seat, his hands and his mouth would alternate breasts, teasing my sensitive curves and hardened nipples to the point that, by the end of the evening, my pussy was so wet and achingly aroused that later, once I got home and into my bed, I could climax with a mere minute or two of furious diddling.

By the middle of July we were dry-humping, and I was more frustrated than ever. Now Scott spent only a minimally polite amount of time on my breasts before mounting me, both of us fully clothed below the waist, and methodically rubbing his lump against my crotch until he panted and sweated bullets and shuddered in a unilateral orgasm. Thankfully, this phase didn't last long.

Looking back on it, I suppose I was a one-girl Sex Education class for him. "Touch me," I finally whispered one hot and humid night as he began to maneuver between my thighs. He inched his hand inside the elastic waistband of my shorts and inside my panties, down across my matted pubic hair until he struck paydirt and discovered how open and juicy I was.

"Jesus," he muttered, a sentiment that I echoed with moans. Soon my shorts were down around one knee and completely off the other leg. Scott's hand was stuffed inside my panties, and his fingers were wandering up and down my labia, encouraging them to blossom into fat, yawning petals. His fingers played in my slickness, meandering from dipping inside my squeezing vagina to strumming across the bone-hard length of my swollen clitoral shaft and its supersensitive little nubbin at the tip.

He was a quick learner and was eager to please. He discovered how to flicker my clit, at first softly, then with greater and greater intensity until my legs strained wide and my butt rose off the seat and my arms wrapped tightly around his neck. My breathing became rapid and shallow and my orgasm would just roar through me. Only then would he reluctantly withdraw his hand and gently stroke his erection against my panty-covered sopping pussy in our Pretend Intercourse position, finishing himself off by a vigorous rub against my pubic bone.

I was in love with him. I was in love with sex.

We didn't stop there, of course. "I want to come with you, Annie," he begged one night with his hand jammed between us and fiddling with my pussy inside my underpants. "Let me rub against you for real," he pleaded. The thought of that sent a ripple of anxiety through my body and a warm rush where his fingers were playing. "I won't go inside you," he promised.

He had my clit trapped between two fingers. I was desperate to come. "Okay," I acquiesced in a small voice.

His fingers withdrew and he fumbled with his shorts with one hand while holding himself up above me with a straightened arm. He got them down to his knees, then maneuvered his underwear down to join his shorts. His shirt draped over his cock. I couldn't see anything. My head was spinning. My back was sweating.

When he eased back down on top of me, though, I could feel it - a ramrod that jutted up and out, nudging against the heat inside my panties. Scott put his hands underneath my shoulderblades and kissed me, breathing hard through his nose. His erection prodded and jabbed at me, trying to find the right angle to rub against me. I tried to adjust my own hips to get him there. We seemed to be in an incredibly clumsy tangle of bodies and limbs and clothes.

"Please let me feel you," he repeated. I knew it was time. I snaked a hand between us, brushing past an alarmingly large and very stiff pole, and pulled aside the crotch of my panties. He sighed, and then I felt the first electric jolt of his warm erection against me, his alive, mysterious thing rubbing against my own intimate folds. "That's it," he whispered, "I won't go inside."

"I know," I replied. Scott brushed against me, and the snagging friction of his dry flesh turned to slippery after a few tentative strokes. His cock notched lengthwise between my lips and he pressed forward, stroking me with the underside of his shaft and sending shivering ripples through my clit that radiated through my pelvis in waves of pleasure.

Scott started and stopped, started and stopped, breathing out little grunts and moans. I was overwhelmed by the newness of the sensations, his heavy body pressing me into the upholstery, the heat boiling off his chest, his turgid flesh and crinkly pubic hair brushing past my fingers, the top of my head edging against the padded armrest, his hairy calf against my smooth-shaven one, the smell of my pussy juices wafting in the air.

And when he quickened his motion and gasped "Oh Annie!" and prodded the tip of his penis higher up and onto my pubic hair, I nestled the crotch of my panties back over his shaft and pressed it against my body, capturing the full force of its spasms as he ejaculated fiery globs against the naked skin of my belly. I could feel the pulses along the underside of his shaft against my clit, and it drove me half crazy. My fingers wobbled his throbbing erection back and forth against my inflamed pussy and then I came, too, gasping and quivering and sharing happy little grunts in his ear.

We got even bolder after that. Scott kept getting better at holding off his climax, and I tempted fate by becoming less and less concerned about pregnancy and more and more enthralled by the sex play and our shared orgasms. Soon he was spurting directly onto my pussylips while I unabashedly frigged myself with his sticky juices, and it seemed like our biggest fear was dripping onto the vinyl upholstery. When I discovered the thrill of masturbating myself while Scott pressed the tip of his cock at the very entrance to my vagina, allowing me to climax before he rubbed himself to his own against my labia, we found ourselves edging progressively away from Pretend and closer to Real.

Holding his cockhead poised at my opening evolved to nudging the mushroom-shaped head partway inside. And that led to getting the entire head inside, and then on another night to penetrating a delicious inch or two. Scott wouldn't move a muscle once he'd worked his way inside me. He'd just insert himself there, his cock erratically twitching, and my fingers would strum wildly on my clit until my body shuddered in those huge cresting waves as my vagina pulsed around his thick intrusion.

The decisive moment came in late August. We were both naked below the waist. I was lying on a blanket, and the other half of it was flipped around Scott's back. I had one ankle curled around his leg, the other foot on the floor. I was spread wide for him. And Scott was finally inside me, completely and totally, and we were both enjoying the sensations of deep slow-motion fucking.

"Scottie," I told him, "Tell me when you're going to come."

"You know I will," he answered with a voice that was dreamy in the world of the back-and-forth trading of his throbs and my clenches. "Annie," he finally said, "Almost there." His erection's involuntary jerks were becoming more frequent. He began to withdraw.

"Wait," I said, restraining him with my legs. "I've got a surprise for you."

Scott grunted an anxious-sounding distracted reply.

"I went to Planned Parenthood," I continued. "I got on the Pill."

"What?"

I had his attention with that one. I tilted my hips and squeezed my legs even tighter around him, capturing his whole length inside me again. His pubic bone was mashed against me, against my magic hard little nubbin. "You can come inside me now," I whispered to him. My hands pulled his butt, and I relaxed my leglock and rocked up against him. "Will you do that for me?" I teased him, "Pretty please?"

He would, and he did. He groaned and drove into me, faster and harder, sending shivers through me every time he bounced off my clit. I felt his rigid maleness, felt his strength and his urgency that matched my own. When he jammed himself into me that one last time and squeezed his arms tightly around me in a primal embrace, I gazed with wonder at his scrunched up face and heard his soft moans and felt the familiar rhythmic jerky pulses in their new unfamiliar surroundings. "I love you, baby," I gasped. I imagined I could feel the hot splash of his spurts, and then in a mad glorious rush I came, too.

Scott and I repeated our back seat coupling only twice more before the cruelty of Fall university enrollments separated us. He left to go back East to an Ivy League school, while I traveled a shorter distance to an in-state university. We reunited over the Holidays and snuck away for a single frustrating quickie. By the following Spring, his parents had moved to the East Coast and Scott spent the summer at their new house, while I lived at home and worked at a local summer job.

We kept in touch, though. We exchanged letters and phone calls. It was more frequently in the beginning, then things gradually declined as we both were busy with school and jobs and, yes, with relationships with other people. In the years after college I moved to the West Coast, got married and later divorced, and Scott remained in the East and also married.

- - - - - -

A few nights later, Jeremy broached the subject again. We were in the afterglow, snuggled together on rumpled sheets, and I was trying to find the energy to move away from the wet spot that was building beneath me. "You never told me your long story," he began. "What makes it 'complicated'?"

I thought about how much to say and how to say it.

"Maybe 'complicated' isn't the right word. Looking back at it, it didn't seem like the typical story of hormonal teenagers in heat. It was more like..." I paused. "It was sweet. It was romantic. I think we really did love each other, way back when."

"But nothing came of it?"

"It was a long time ago. We went our separate ways." I paused again. That part was true. We did go our separate ways. At least we did for a decade, until Scott traveled West for a Bar Association conference. After we had dinner together, reminiscing, we skipped dessert and went to his hotel room. That night was the first time he and I had sex together on a bed. And it wasn't the last time. Over the next two decades, every few years one of us traveled to the opposite coast, and we'd spend a few hours together, or a few days, reconnecting minds and bodies.

Now, as I felt Jeremy's semen leaking out of me, I remembered how Scott's had done the same three months earlier when we'd made love on another bed 30 miles away with the sound of cable cars clanging on the street below. The truth was that what was 'complicated' wasn't what happened during that distant summer after high school, it was what had been happening ever since.

I leaned forward and kissed Jeremy, then rolled him onto his back and slipped on top of him, straddling his hips. "Carpe diem," I told him, brushing my dripping pussy against his deflated penis. His hands cupped my breasts, and I smiled and added, "Carpe boobs works, too." He laughed, and I knew everything would be all right for another day.