tagFirst TimeTaralee's First Time Ch. 03

Taralee's First Time Ch. 03


Sex was my undoing.

I was desperately in love with two guys. I was fucking Pierre whenever he could get away from his over-vigilant mom. Danny, I was fantasizing having hot sex with. And I was regularly getting a good licking (usually followed by a rhythmic, legs-spread thumping, just to make sure) from Ken, a friend of my sister who was in his mid-twenties.

I had no one I felt I could talk to about the details of these affairs, not even my best friend Jess. I found it impossible to share what, in my darkest moments, seemed sordid and dirty. And somehow I found it impossible to say No when opportunity (in the shape of stiff penis) arose. Even when my head said I should.

All this confusion had the inevitable effect on my grades. I did okay on my PSATs, but I had to do something: second semester Grade 11 grades were the ones that counted for college admissions, and two months before my nineteenth birthday, mine were looking worse and worse. I knew I had to buckle down.

Luckily Ken got some work with a contractor out of town, so that cut out one temptation for a while. Then Pierre came down with mononucleosis, "mono." My school friends laughed that he'd caught what had a reputation as the "kissing disease" — that much they knew about what we were up to every day after school. But when his doctor condemned him to six weeks of bed rest, I missed him sorely. His mother and I really didn't get along (she'd figured out what was up between us, no surprise) and she barely tolerated brief, twice-weekly visits when I brought him his homework and picked up his completed assignments.

He was going crazy too, and if I was at home when his folks went out he'd go into their bedroom, lie on their bed and phone me (no extensions in their little apartment), jerking himself off while I put the phone between my legs so he could hear the squishy sounds as I got myself hot with a couple of fingers and a vivid imagination. Once he said his parents came home unexpectedly and he nearly got caught wiping sperm off the picture that hung over their headboard because he'd shot four feet! I envied him like hell: although I could work myself into a frantic state of drenched horniness by massaging the hard nub of my clit and my reddened, swollen labia (oh yes, I still had that bedroom mirror propped against a wall and watched) I could never achieve a climax, collapsing instead in near-tears frustration, cursing Pierre's doctor and Ken's job.

Mostly, though, I hit the books, even when I was babysitting. I had a couple of neighborhood brats I looked after regularly, and half a block away from my house a lawyer, George, and his wife Virginia would hire me from time to time when they went out to the theater. Their four-year-old twins were little hellions, but they paid twice the going rate for four hours' work and once the twins were in bed, I could use his den to study, which started to bring my grades up.

In March, George left a message with my mom: his wife was out of town looking after her sick mom for a couple of weeks, and could I mind the twins in the evenings after their housekeeper left for the day? The money would help my college fund and I'd be able go home at eleven and get a good night's rest before school the next day.

The first few days were uneventful, except for a couple of hair-pulling four-year-olds' tantrums. My study routine was working out, and I left a couple of books in the den so I didn't have to lug them back and forth.

One evening as I was grinding my way through a particularly boring chapter in my history text, George knocked gently, stuck his head in the door and asked if I'd like a Manhattan. I wasn't sure, but I didn't want to turn down friendly hospitality from a man who paid handsomely for me to make supper for his little darlings and put them to bed. I was mildly surprised when I saw he was wearing a stunning deep purple robe with black silk lapels; it looked like something I'd seen in movies. He was a handsome man with dark hair just graying at the temples, a square jaw, laugh lines and dancing gray eyes.

He moved confidently to a mahogany trolley that held decanters and a silver ice bucket. I hadn't noticed the condensation: it had been filled recently. Cubes clinked in two heavy glasses, George poured dark liquids and stirred gently with a long silver spoon, then dropped a cherry in each glass and handed me one. At the first sip I spluttered and coughed, my tongue burning and eyes watering, so he came over and patted my back gently, leaning against the desk. The second sip was better and by the third, the elixir was having an effect.

His smile came into focus close beside me, and the world seemed like a warmer, better place. When he put his arm behind me, my inhibitions loosened and I snuggled into his shoulder. The silk of his robe rustled enticingly. His hand slid lightly up my back under my blouse, and expertly unclipped my bra, liberating my breasts and setting my heart a-flutter.

My dad had been right about candy and liquor.

George's strong hands slowly drew my blouse over my head and pulled it off my arms. His lips ensnared my left nipple and his tongue, hot from the bourbon and cold from the ice, flicked it till it stood out hard. Weaving gently from the liquor, I stood unprotesting while he unbuckled my belt, unzipped my jeans, slid his thumbs inside my panties and smoothly pulled everything down around my ankles.

I stepped out obediently.

His palms cupped my swelling breasts then slid down my belly. His fingers toyed with my pubic hair for a few moments, then, sensing no resistance on my part, he pushed me slowly, ever so slowly, down on the leather-topped desk and stepped out of his robe.

George was no boy, he was a robust, supremely confident man.

As I lay back he held my legs up in a wide V and I stared through them at his muscled chest and flat belly. In a large, dark mirror on the wall behind him I could see his tight buttocks and wide shoulders, his big hands holding my pale legs in the air. Looking down, I was mesmerized by the curly black hair around his rigid, uptilted cock. Its shaft was roped with thick veins and it was bobbing just above the light brown hair on my mound of Venus.

I could already feel juice dripping from my cunt, ready to welcome what I now wanted so urgently! He bent slightly forward, stretching my legs wide with his strong arms.

But he just laid his rigid member between the swollen, wide open lips of my cunt and started sliding it up and down, ever so slowly. It was burning hot and felt as if it were lighting a fire in my belly. Every time its purplish head touched my clit I jerked, until all my muscles started to tremble. But he was careful not to stick it in me. He could feel my climax coming and leaned down on me, pressing his balls against me as his cock slid back and forth, as the old blues song said, like "a hotdog in my bun."

"Put it in! Put ... It ... In," I begged. To no avail. His deep, ragged bass said, "No, Taralee, not now."

Suddenly my vision went dark, fireworks blasted across my eyes and my juices flowed and he felt me shuddering at my climax and his weight sagged on top of me. I felt his thick, iron-hard penis jerking and hot jism spurting again and again and again and again onto my belly.

Panting heavily, he slowly pulled back, kissing my now-tender nipples and spreading the puddle of semen across my belly with his fingers. Afterwards he brought a steaming hot Turkish towel and cleaned me up, then helped me back into my clothes. It was eleven, time to go home. He watched as I walked down the street, standing on his porch till I was safely inside.

In my bedroom I counted my babysitting money and found a tip four times what I'd earned.

Was I now a prostitute, I wondered?

No, I rationalized, I enjoyed that way too much.

George and I had several more assignations before Virginia got back. He'd make me a Manhattan then slowly undress me. Dropping his robe he'd wrap his hand around his stiffening cock and stroke it till it stood up proud with its purplish head swollen and glistening, then pull on a Forex prophylactic. They were made out of "lambskin" he said, and the sensation was like wearing nothing at all. He assured me I needn't worry about pregnancy — a good thing, because he'd ejaculate a few tablespoonfuls each time— and to me they felt so much better than the slippery rubbers Pierre and Ken used. The extra heat and friction, and that network of hard veins that roped around George's cock, brought me to several climaxes each time we made love.

I tried some of those Kama Sutra positions Pierre and I had used: George specially seemed to enjoy the view of an eighteen-year-old girl kneeling on his desk as his erection slid in and out between the cheeks of her ass. I'd turn around and watch him watching me, and get hotter and hotter the more I saw his pleasure as his rhythm built up speed. Once I thought I saw movement in that mirror behind him, but it must've been my long hair swinging with my movements.

A few weeks later, after Virginia returned, she phoned to say they had tickets to the ballet and would I mind the twins? Pierre had just been sprung from his six-week sentence for mono, and was randy as hell. I invited him to "study" with me.

Not only had George given me explicit permission for him to visit, but he'd said to celebrate Pierre's return, let him wear a Forex, he'll love it. They were a very expensive luxury, and Pierre shot me a quizzical look when I went over to George's desk, opened the box and took out the blue plastic cylinder.

But if he was suspicious, he didn't ask. And I didn't tell.

Pierre was thrilled by the Forex experience, though he did mention it had a slight formaldehyde smell (he was, after all, planning to major in science in college). The sensation, he said, was the best. And I agreed. We actually used two lambskins. The second time, I got Pierre to lean between my spread legs as I sat on the edge of George's desk, straddling him, kissing him, feeling my breasts mashed against his chest and our breaths coming in unison as that lovely penis slid so far into me it touched my cervix, sending sent electric shocks through my whole body.

I opened my eyes to watch us in that dark mirror and this time I really did see a glimmer of movement beyond our thrusting, straining bodies. Awareness dawned: a two-way mirror. George must've come home and was watching us. I could see a shadowy movement and suddenly realized he was stroking his cock in rhythm with us. The idea of him whacking off watching Pierre fuck me made my muscles clench and sent us into a simultaneous quivering, shuddering, fireworks-exploding climax.

Around this time my mom surprised me by offering to take me to her gynecologist. I'd been plagued by irregular periods, which often gave me cramps so bad I'd be doubled over in the nurse's office at school, moaning and rocking myself in agony. (Secretly I'd hoped that losing my virginity would help, but that turned out to be an old wives' tale.)

I took an afternoon off from school and with some trepidation sat with mom in the waiting room. When the nurse handed me a gown and told me to disrobe, my discomfort grew. But mom had assured me that the obligatory Pap smear wouldn't hurt anything more than my dignity. So moments later I was lying back, my legs spread and ankles in ice-cold metal stirrups, with my vagina wide open under glare of an examination-room lamp. It was the unsexiest moment of my life.

The gynecologist was a woman (thank God!) and empathetic, and the procedure didn't take long. But I was acutely uncomfortable lying there with my legs apart and a stranger fingering my labia and clitoris, inserting a freezing cold speculum, and talking about my sexual health. I admitted to her that I was "sexually active" and had a steady boyfriend, but let's just say I kept to a rather censored version of my sex life so far.

Then I sat nervously in the waiting room for a quarter-hour, while she consulted with my mom in her office. She returned with a prescription.

For ... The Pill.

Welcome to the Swinging Sixties!

I was elated but disturbed, too. Would there be side effects? Could it make me more promiscuous (was that possible)? Would I gain weight?

The doctor's instructions, relayed by my embarrassingly clinical mother, were clear: The Pill had to be taken at the same time every day for twenty-one days, then started again a week later, presumably after my period. No forgotten pills, no skipped days.

And wait a month before having unprotected sex.

This was not a conversation I enjoyed, but at least my mom was patient, kind and non-judgmental. I was pretty quiet on the bus ride home, but mom held my hand and I felt secure, though my mind was a whirl of images — Pierre, Ken, George, and yes, Danny — my secrets fizzed inside me until I felt I could burst with from untold secrets.

As spring rushed into Washington with cherry blossoms around the Tidal Basin and the first sultry nights, the benighted administration at our high school moved to censor the annual poetry magazine. That brought one of my first experiences with 1960s collective activism: A bunch of us got together to publish our own, uncensored literary zine. In a couple of weeks we had as many submissions as we could publish, had raised enough money to buy paper and had secured the loan of a Gestetner duplicator. Pierre and a couple of other students with access to electric typewriters beavered away making the stencils, while a couple of art students decorated the inside pages and came up with a cover design.

Production night was memorable. Maybe twenty high schoolers crowded into the second floor of a small, ink-scented downtown industrial space that the Gestetner shared with a couple of larger printing presses. A petite, curvy girl who was finishing high school part-time, after dropping out a couple of years earlier, welcomed us. It was warm in the place, and she had on a flimsy top and the shortest skirt I'd ever seen (except for the micro-minis that were starting to show up in English magazines). We didn't know Cathy well, but she'd arranged the printing for us. She lived on the third floor with two tall guys whom we didn't know at all.

The guys showed us how to set up the machinery and mount the stencils for each page. The room was filled with a cheerful cacophony of the clattering duplicator, the chatter of the crew collating the pages, the thump of the stapling machine and the excited shouts of students carrying boxes of finished magazines down to the cars waiting in the street.

Cathy oversaw the production, giving tips here and there, showing us where the ink and supplies were, and generally being helpful and kind. She tended to distract the guys — and some of us girls: It was obvious she wasn't wearing a bra. Her large round breasts bounced as she walked, her prominent nipples poked through the thin fabric of her top and the globes of her ass swayed seductively as she walked. She didn't seem to mind our stares.

About an hour later the printing was done, leaving just the collating, stapling and boxing of the last couple of hundred of magazines. "Okay," she shouted, "y'all finish up and lock the door on your way out.

"Time to mount the stairs, boys," she said, grabbing both of the tall guys, one in each hand, and leading them to the ladder-like steps that led up to a hatch in the ceiling. I felt Pierre's grip on my hand tighten as the trio got halfway up the steps and she turned toward us with a broad smile to bid us goodnight. Not only was she braless, but she was wearing nothing under her skirt, either, and we all got a sumptuous flash of the dark bush between her shapely legs as she led her two paramours up to bed.

Fortunately Pierre had managed to loosen his mother's apron strings and had permission to stay out all night. Once the last box of zines was packed, we locked Cathy's street door and jumped in the old Ford wagon. He had his fingers between my legs in seconds. I was sopping wet, thinking of Cathy in bed with her two tall guys and imagining what it would feel like to have then take me turn and turn about, each one getting hornier when the other came.

But I made Pierre wait: I had a surprise for him. My brother was out of town and he'd left me the keys to his loft, just a five-minute drive from Cathy's place. We parked the Ford and raced up the stairs. It was our first night sleeping together.

"Imagine that I'm Cathy," I said, sliding my panties off and lying back with my skirt pulled up just high enough to show a tease of pubic hair. Beside the big bed there was a bowl full of prophylactics — thank you, dear brother! — and Pierre dropped his jeans, tore one open and unrolled it over his delicious, stiff cock. I lifted my knees to open my dripping cunt. He pulled me to him and we fucked like animals, urgently, sideways on the bed, my skirt rumpled around my waist and his jeans around his ankles.

Oh God, how I loved his penis ... his smooth, perfect glans slid into me and then the hard, wide part of his shaft stretched my G-spot and sent the fireworks exploding through my brain. He pumped me like a madman and we came in unison after only a couple of minutes, then lay there gasping and laughing till we caught our breath.

Our lovemaking seemed to go all night and too soon the morning sun flooded the little apartment. I awoke first, Pierre's arms around me, and moved softly so I could stare at his face and his beautiful eyelashes and perfect ears and the quadrillion freckles sprayed across his face and neck like the stars in the Milky Way. My heart beat in unison with his and I wanted so much for that moment to last. At least it was Saturday, and we didn't have to get to school by nine o'clock.

For my birthday — my last as a teenager — my brother, ever the funny guy, got me an expensive pair of black fishnet stockings. Which I loved; Pierre, too, needless to say. They were sexy as hell, but my ego took a battering every time my sardonic dad saw me come down the stairs wearing them: he couldn't resist calling them (with a wicked grin), "whore stockings."

Pierre's gift was a gorgeous leopard-print bathing suit. Stretchy, with daringly high cut legs and a scoop back, it sure maximized my assets, such as they were. I didn't think I'd dare wear it at the beach, and I wasn't going to let it anywhere near the over-chlorinated high school pool — or the bitchy girls who hung around it with falsies stretching the tops of their heavy knit one-pieces.

Finally, the weather turned summery, but with the change came exams at school. Pierre was studying really hard — though he'd already been accepted at a good college, he was taking advanced-credit courses that would give him a head start when he got there and he wanted high grades. And I was desperately trying to bring my grades up, haunted by forebodings of a miserable life in a suburban steno pool. We spent several weeks with no more intimacy than holding hands while we both studied in a sunny courtyard at school.

But eventually we reached the home stretch. Pierre rode the green D.C. Transit bus with me after school and carried my books as we walked down the well-treed street to the warm, wonderful old house with squirrels in the attic and so many memories. I threw together a stew and put it in the oven (my chores were to make the family's dinner while mom was at work) and Pierre and I each grabbed a book and headed across the little creek to the big hilly estate that was our teenage paradise.

Someone had mown the meadow and the warm air was full of the sweet scent of fresh-cut hay. Hand in hand we ran and laughed and, books forgotten, tripped and rolled over and over down the hill like two five-year-olds, ending up in each other's arms. "Roll me over, in the clover," I crooned, looking up into Pierre's freckle-framed blue eyes. "Roll me over, lay me down and do it again."

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