Ten Illustrated Stories About First Time Sex

Funny, sad, and nostalgic tales submitted by Nerve readers.

A year ago, we started collecting your stories about having sex for the first time. Some of these have been hilarious, some awkward, some sad, and some sexy. All of them have been honest. Here are our ten favorites. Do you have a great first-time story? Tell us! My First Time runs every Tuesday on Nerve.com.

1. "I zeroed my sights on a bassist…"

Female • 17 years old years old • Pennsylvania

I celebrated the end of my junior year of high school with my ultra-cool, apartment-renting, punk-rock-music-educating, twenty-one-year-old boyfriend dumping me. Later, I found out the reason — I didn’t put out.

### Illustration by Thomas Pitilli

So when I ended up at a local punk-rock show he was also attending a scant few months later, I decided jealousy was the best weapon. Using my sweet-ass vintage Wonder Woman t-shirt and the kind of perky boobs only a girl of seventeen can possess, I zeroed my sights in on Dan, a bassist who spastically jumped and thrashed through his band’s set of three-chord, throat-punishing songs. He was also shirtless, except for three pages torn from Hustler, adhered to him by his surprisingly sticky sweat.

But what made him perfect, despite the fact he only topped a hundred pounds when holding his bass, was the fact that he was friends with my ex. I’ll show you who’s frigid.

I don’t think Dan and I ever went on any outing you could actually classify as a date, but if we had, I approximate I gave it up on date three. We were in the cinderblock basement of his mom’s house, in a room made tough with liberal use of duct tape, band stickers and the central placement of his bass. Of course, his mother and still-elementary-school-aged sister could easily be heard moving through the rooms above us.

###After making out moved us from recliner to mattress, we conveyed to each other through a series of head movements and meaningful glances that tonight was the night — no more V-card. While he fumbled around looking for a condom, I pulled my jeans and panties down, but left on my tank top, half because I was still so shy about my body and half because the chilly basement temperature.

Then he was on top of me… and then I think he was inside of me? My virginity, the last of its kind in my circle of friends, had been lost in under thirty seconds. Still above me, Dan leaned back and whispered, "It gets better than this."

I stumbled to the bathroom to clean myself. I came back to find Dan lounging in the recliner, staring blankly at the TV. We spent the rest of the night watching a marathon of the dating show Change of Heart. It would take weeks — weeks curiously void of any other attempt at intercourse — for the irony of that entertainment choice to sink in. I’ve never tried to make a man who dumped me jealous by trying to fuck his friend again.

NEXT: "The first time we went out ended in handcuffs…"

2. "The first time we went out ended in handcuffs…"

Male • 16 years old • Houston

I was a girl-crazy junior in high school when I noticed a sophomore who was in two of my classes. She was a swimmer with a great toned body and sexy eyes. We started to hang out in the same group of friends and quickly it was clear there was a mutual attraction. The first time we went out ended in handcuffs, a misdemeanor charge for criminal mischief, and our parents coming to the police station to pick us up. Not the ideal first date, but I guess it was foreshadowing things to come.

### Illustration by Thomas Pitilli

Our parents did everything they could to keep us away from each other, which just fueled our determination to be together. We made out in the back stairwell at school and in parks after dark, and we’d sneak out to meet in the middle of the night. We couldn’t keep our hands off each other, but neither of us ever had a condom, so we both remained virgins.

I finally bought some condoms and we agreed to meet in the parking lot around lunch and skip school that afternoon. Our options for privacy were limited. We couldn’t guarantee either of our houses would be empty and my little Nissan wasn’t exactly spacious, so we found an empty cul-de-sac in an abandoned development away from everything. I parked the car and spread out a blanket on the rough field grass. We took off our pants, and I fumbled with the condom until I was finally in.

###In what felt like ten seconds later, we heard a car coming down the abandoned road — not just any car, but a police car coming to interrupt our little party in the middle of nowhere. Unlike Seth Rogen in Superbad, the female police officer had no problem cock-blocking me, and after we got dressed she took the swimmer in for truancy because she was under sixteen. After her mom got the second call from the police to pick her up, we had to get even more careful about tricking our parents. But we were able to stay away from the police, and the extreme efforts turned out to be worth it.

NEXT: "Under false pretenses, three-thousand miles away from home…"

3. "Under false pretenses, three-thousand miles
away from home…

Female • 17 years old • Los Angeles, CA

In an admittedly self-righteous and rebellious moment, I decided to hop a train from the comfort of my seaside high-school town to visit a friend who was at a state university. I thought only about two things on the way up: make-out sessions with college sophomores, and how delicious all of the vodka concoctions would taste on the way down.

But what I got was far more enthralling. At a college rager, amongst waves of red cups and cigarette butts, I met someone who would become the first love of my teenage life. He was from Los Angeles, black-haired, clad in vintage specs and a white t-shirt. He screamed badass.

### Illustration by Thomas Pitilli

I was seventeen and indescribably smitten. I didn’t have to think twice about ditching my friends, and spent the rest of the weekend trying to impress and out-cool my new beau. Before him, I’d never wanted to give anyone an inch, let alone a mile. But I was a frequent masturbator, and figured I was so in touch with my own body and sexuality that as soon as I let someone else explore, all those years of pent-up sexual frustration would erupt out.

I started living for weekend trips, sneaking off to the city for heavy petting in the park and quiet time at the museum. I couldn’t think of bringing anyone home to my house in the suburbs; the idea of losing my virginity upstairs from my parents’ bedroom seemed way too cliché for how I normally did things. I was a little more creative than that. So, I devised a plan for spring break to fly on my own dime to L.A. to visit an old friend and simultaneously check out some West Coast schools. My bohemian mother bought it, and soon I found myself flying across the country, alone, into the stardust city lights of Los Angeles, free and scared shitless.

Under false pretenses, three-thousand miles away from New York, I roamed around a foreign city, grinning at the realization that I’d actually pulled this off. Everything about the scenery seemed cooler and more dangerous than anything I’d ever experienced in my adolescence in NYC. We were staying at a pay-per-week motel in East Los Angeles, and no sooner had we checked in than I had him on the floor. We made out until our clothes were scattered about the room. On our way to the bed, I made him turn off the lights.

###I wanted to try all of the positions my friends had bragged about. But they seemed pretty impossible for two chaste virgins in the dark. I wanted to be graceful, legs propped up like an umbrella, bent backward, sitting, standing, stretching. Instead, I had his body resting heavily on top of mine while he tore at my insides. I didn’t cry, although for about two hours after the fact I wanted to do nothing but.

It wasn’t romantic, and the blood spots certainly didn’t make it seem beautiful, but there I was, in the throes of hysterical first love, in a new city with the most interesting person I had ever met, naked and free. The rest of my time in Los Angeles was a blur of moments captured in Polaroid memories. Despite all of the madness that followed, I still look back fondly and can’t believe I got away with any of it.

NEXT: "I was the only person who’d ever befriended her before trying to get her into bed…"

4. "I was the only person who’d ever befriended her before trying to get her into bed…"

Male • 18 years old • Suburbs of Philadelphia

We met through a mutual friend she’d been fucking at the time, the night before the dorms closed for Christmas break. She’d come over to our dorm from the all-girl college she attended nearby. Our mutual friend was generally stoned and generally preaching whatever philosopher he’d been reading in whatever class he was failing at the moment. That night, it was Nietzsche, and his barrage of two-bit words made it even less sexy than usual. We ran away and snuck up onto the roof to smoke a cigarette and talk about the sex neither of us would be having that night. We came down hours later, our friend passed out on the dorm couch, so I drove the girl to a diner, and eventually to the airport.

### Illustration by Thomas Pitilli

I’d always had lots of female friends; I got along well with girls my age, but always as friends. She was quirky, odd, eccentric, but beautiful. She looked like one of Tolkien’s elves, and her openness lent her this air of mystery. It seemed too easy to connect with her, and admit our mutual physical attraction. I thought she was crazy, but it only made me want her more.

Over break, we talked incessantly via email, and I had a feeling that it wasn’t going to be too hard to get her into bed. I fancied that I was "playing" her, but was really falling in love with the idea of losing my virginity to someone who wasn’t drunk. I even felt bad about plotting to get into her pants. I was supposed to be a nice guy, and a reliable friend.

I met her at the airport in January. She’d had trouble with family and several ex-boyfriends back home. I drove her to her dorm, carried her bags into her room, and threw her up against a wall. She attacked me with a ferocity I’d never even seen in films. I found out later that I was the only person who’d ever befriended her before trying to get her into bed.

###We kissed, and fell into her bed. I awkwardly undressed her as she squirmed against me, trying to do the same. She sheepishly admitted she’d worn "granny panties" because she hadn’t wanted to sleep with me, but I was so excited I couldn’t even tell what color they were. She had been a long-distance runner, and her body was spectacular. She had condoms, but had been recently tested, and was on the pill, so we didn’t use one.

I entered her, and as she rocked against me, she called me by my hippie-stoner philosofriend’s name. I tried to ignore it, but it happened several more times, and I couldn’t finish. As I dressed, she apologized repeatedly, crying and telling me to spend the night. She hadn’t meant to call me by another name, it had just slipped out. When I declined, she started undressing me again, so I went back to bed. This would be a pattern for us over the next year and a half. I was her anchor, just as her sex was mine.

NEXT: "I lay back in the hammock and he carefully climbed on top of me…"

5. "I lay back in the hammock and he carefully climbed on top of me…"

Female • 17 years old • Rio Grande Valley, TX

I’d always been eager to learn about sex. I was snatching my mother’s romance novels at ten and reading them cover to cover in the bathroom. I’d snoop in my older brother’s porn collection and shudder with revulsion at the overly large breasts and creepy, staring, eye-like nipples. I used to imagine that the gigantic breasts were some sort of extra bladder for pee. (I know, I was a weird kid.)

As I got older, I would read Cosmo and Glamour to learn "88 ways to blow his mind," look up words like "coitus" and "clitoris" in the medical dictionary on my dad’s shelf, and sneak hurried glances at the naked women in the public-pool locker room. By senior year of high school, I was known for my sweet face and dirty sense of humor. Through all my research, I’d amassed a lot of sexual knowledge without any real experience. With two kisses from two different guys, one boob touch, and half a blowjob, I was basically all talk, no walk. I would joke that I planned on selling my virginity on eBay and retiring at nineteen, but really I was just hoping I wouldn’t graduate a virgin.

I started dating my boyfriend early second semester of twelfth grade. He had considerably more sexual experience than I did, but I wasn’t worried. I knew everything there was to know, right? Thanks to our almost instantaneous emotional connection (high school is good at creating those kinds of relationships) and crazy chemistry, we progressed quickly from making out, to boob grabs, to handjobs, to blowjobs, to manual stimulation of my nether-regions. We had to be careful not to get caught, so much of our time "watching TV" in the den with the lights out, or "talking" outside after dark was really put towards our sexy checklist.

### Illustration by Thomas Pitilli

After two months of dating, and a ton of research on my part (brands of condoms, the effectiveness of the "pull-out" method, careful observation of my cervical mucus for clues to my ovulation cycle, and the effects of low BMI on fertility), I felt suitably prepared to relinquish my V-card. First, we started off with little "experiments" — just casual, introductory, "Hi, I’m a penis" meetings with my vagina. These would take place on my family’s trampoline in the backyard, in the dark. About an inch would go in and we’d pause to see how we both felt, and then go another inch in. This would continue until I would hiss with pain and smack him on the arm to "pull out, you dummy!" He was a cut seven-and-a-half inches, so we’d make it about half-way in.

I never worried about breaking my hymen because I had actually accomplished that in the first grade by falling out of a tree. I just wanted to make sure my vagina would be receptive to the whole "penetration process." I’d heard awful stories of women experiencing unimaginable pain during intercourse, women who bled for ten minutes straight, women whose lovers found "growths" or "lumps" in their vaginas that turned out to be undescended testicles. All of this was "totally true" and happened to "my friend’s cousin’s massage therapist’s niece’s bunk-buddy at church camp, I swear!" but eh, I was naive and paranoid, so I proceeded cautiously.

When we finally did the deed, we did it in the big, green hammock on my patio, next to my dad’s jasmine vines. It was one of those stand-alone hammocks — no trees necessary! — and surprisingly sturdy. My siblings were all asleep inside, and my mom had dozed off in front of the TV earlier. I’d changed into a short gray skirt (for easy access) and crazy-patterned knee-socks (for fun). He wore regular clothes and threw his belt into the grass. The condom? Trojan, Twisted Pleasure. I lay back in the hammock and he carefully climbed on top of me. I took deep breaths of the jasmine-scented air and tried not to be nervous. I could see the moon over his shoulder and I remember thinking, "This is right. I’m glad I waited."

###I helped him put on the condom (being sure to pinch the tip), and kissed him over and over again. With my hand guiding him in, we finally had real, complete sexual intercourse. The hammock swayed with his thrusts, making me dizzy, but I got used to it. It started to feel really nice, like a foot-rub for my vagina. I didn’t come that night, because I wasn’t quite sure how to come from intercourse. I understood the dynamics of clitoral stimulation, but I wasn’t sure how I could get a hand in with him on top of me.

Afterwards, we declared it a success. I was no longer a virgin! I felt a little regretful, mostly because I had a residual childhood belief that unicorns existed and only appeared to virginal maidens. (I told you I was a weird kid.) But I’m still with that boyfriend and we’re very happy together. I can totally come from intercourse like a pro. A moonlit night in spring, in a hammock, with a guy I loved? I think my first time was perfect.

NEXT: "I was fifteen and fighting with every ounce of my power not to be gay…"

6. "I was fifteen and fighting with every ounce of my power
not to be gay…"

Male • 15 years old • New York City

The first time I had sex… well, almost had sex — I’m counting it because it’s the closest I ever came with a woman — was in the mid-’80s (of course it was), in the back room of a strip club off Times Square, with a dark-skinned hooker called "Baby," who, true to her name, reeked of the powder-fresh goodness that can only be found in a bottle of Love’s Baby Soft.

### Illustration by Thomas Pitilli

I was fifteen and fighting with every ounce of my power not to be gay. This brought me here, two-and-a-half hours south on the bus, to a sad little side room with a mattress, an apple crate, and — I don’t exaggerate — a lamp with a bare light bulb and no shade. There, I listened as my best friend and object of my every secret carnal desire, George, lost his virginity, quite loudly, with a German named Daisy, just opposite the wall to my right.

My heart could barely stand it. I thought he was like me. Hadn’t he too been dodging and shifting around in his make-out sessions with girls, petrified a fumbling hand would land on an obviously soft penis? "What’s wrong?" "Are you okay?" I’d cover with everything from a stomach ache to Catholicism, knowing full well this was another girlfriend I’d never call again, number seven on a sexual-amends list that was projecting way too far in the future.

I was always hoping something would stir in my pants. I wasn’t cruel — I liked these girls. I kept waiting for one to fix me. I’d hoped two weeks ago it was Marlene. At a pool party, I pulled her aside for five minutes of carefully orchestrated "Oooo, this is so hot, we could get caught" time so I could fingerbang her and gauge just how I felt. (Sad, and like I needed a Wet-Nap.)

This was my last-ditch effort. Baby looked like Coco from Fame. I thought she was exquisite. She looked at me and smiled and I lifted her chin and kissed her. It was sweet, which I knew was probably wrong, so I pressed down hard with passion. I took her pretending she was George, not the George in the next room but the one who’d ask me for a T-shirt to borrow. I couldn’t get past my nerves, the voices of coaches, of brothers, of God, the pressure exploding in my head that made everything go limp down below in my loins. I truly believed if I couldn’t perform with Baby then I might as well pack it in.

Finally, I stopped. I couldn’t avoid Baby’s hands any longer. Nothing she did made a difference. My dick was a dismal wreck. There was nothing to do but roll off her, and crumble in a ball at her feet.

###"You gay?" she asked in a voice so soft she was my mother.

"Yes," I said simply, before I could think. There it was, no denial, in front of me, for the first time out loud, for someone else to judge and to mock me.

"It’s okay!" she practically screamed, dismissing my angst so succinctly I had no other choice but to believe her. Baby was wise to the future. I heard taxis and laughter and night. George was finally quiet, I heard city and possibility, and I smiled. It was okay. Best money I ever spent. Baby showed me it’s okay.

NEXT: "The nightclub was packed…"

7. "The nightclub was packed…"

Female • 17 years old • New York City

It was a blistering cold January night in 1989, and The World nightclub was packed with drag queens, homeboys, and all sorts in between. In typical Saturday night fashion, my homegirls and I were dancing and soul-clapping the night away to tracks like "I’ll House You," "Jack Your Body," and "Work It to the Bone." I was in the middle of bustin’ a move when SJ approached.

### Illustration by Thomas Pitilli

SJ wasn’t my boyfriend, but I wished he was. To seventeen-year-old me, he was as exotic as they came: Italian and Jewish from Bensonhurst, crazy green eyes bordered by Ken Wahl-esque brows and even crazier thick, full lips. I loved everything about him — his "danger", his club connections, and how he knew all the rhymes to "Ain’t No Half Steppin’" by Big Daddy Kane. But, mostly, I loved his scent, a blend of Obsession for Men, weed, alcohol, and sweat. We’d danced a bit when he leaned in and whispered, "We gonna chill later, right?" Then, off he went, plying his trade to the party-going smokers and sniffers. I turned back to my friends and grinned like an idiot, much to their irritation. None of them liked him.

A few hours later, closing time was fast approaching and my friends wanted to go home. But I impatiently awaited SJ’s return. Leaving now was not an option. "What are you gonna do? Stay here?" Mira screeched. "Look at that fucking line for fucking coat check."

Just then, SJ surfaced from behind me and slipped his arms around my waist. "Yeah, yeah, I’ll be fine," I said, and shooed them goodbye. The bouncers made their final rounds, clearing out the club, ignoring the two of us as we sat on a couch — SJ had carte blanche with club management because he brought in so much business. I was already giddy from a night’s worth of complimentary Sex on the Beaches, so a couple of tokes from the joint he’d rolled rendered me thoroughly zooted.

I started to shiver and he asked, "You cold? We gotta fix that." He pulled me up onto his lap, facing him, and we started to make out. When I felt his jimmy perk up, I reached down for it, and he said, "Let’s go upstairs." We climbed two floors up, to the far corner of a balcony, and continued our groping session. As he pulled down my biker shorts and his track-suit bottoms, I searched my baby brother’s Ninja Turtles lunch box, which doubled as my party bag, and produced a rubber.

After months of heavy petting, I couldn’t believe it was about to actually happen. I was petrified, and I’d always imagined my first time being just a little more romantic, but I was excited, too. He fumbled to put the condom on and subsequently fumbled to put his penis in. When he did, I saw stars. I gasped and trembled in pain as my hands clutched onto the back of his neck. Nothing had ever hurt as much as this. "It’s okay, baby," he murmured. Not really, I thought. After a few moments, he moaned and was still, then stepped backward. I felt a hot liquid trickling down my leg. I feared the condom had broken, but in the dimness, I could see that it was blood. "I’m bleeding," I said blankly.

He grabbed napkins from behind a deserted bar. "Why you always bleedin’ every time we chill?" harking back to a night he’d stolen a box of tampons from the now defunct Store 24 on Greenwich, after I’d explained to him why he couldn’t put his hand down my pants. We pulled up our clothes. I really wanted a cigarette, not in the clichéd post-coital way, but for something to do while my mind replayed what had just happened. When I lit one he said, "That’s a real nasty habit." I looked back at him, dazed as he took the cigarette from my mouth and took one long drag.

In the coat-check room, we discovered that my coat had been stolen. My eyes welled with tears. He chuckled and said, "Aww, don’t cry, girl. I’ll find something in the office. Mad people be leaving things here." When he emerged, he handed me a tattered and matted black-velour cape. I put it on.

###We got outside, and the sun was coming up, but it was still freezing. He put his arm around my shoulders and we walked towards 1st Avenue silently until he offered to buy me breakfast at McDonald’s. I shook my head. All I wanted to do was to go home, take a shower and put on the flannel PJs mommy got me for Christmas. Oh, shit, mommy! She was gonna shit bricks. She was definitely up and getting ready to go to work. Man, I hadn’t thought of that.

My mind reeled. "You have money?" he asked. I didn’t. "Why you go out with no loot? That’s not safe." He pulled out his wad of cash, handed me some money and hailed a cab, telling the driver, "Yo, take this girl to the Bronx, all right?" Before the driver pulled out, SJ tapped on the back window. "If you go out this week, give me a beep." I went out, I saw him, I beeped him, but he never called back.

NEXT: "We wandered around West Philly in the rain, looking for a good place…"

8. "We wandered around West Philly in the rain, looking for a good place…"

Female • 17 years old • Philadelphia

When I first saw The Boy, I wanted it to be him. He had these puppy-dog eyes that turned down slightly at the corners and he wore tight jeans and listened to indie rock and his brother was a famous TV star. It felt like the plot of a horribly quirky indie film just waiting to happen. Naturally, I assumed that simply because he was so ideal, there was zero chance of it happening. I was certain I would instead lose my virginity at a party, drunkenly half-raped by any pretentious cigarette-smoking English major who happened to wander my way. Luckily or not, it didn’t end up like that.

The Boy was my best friend, and somewhere around ten-thousand Facebook messages after meeting him, two seemingly innocuous things occurred simultaneously. I got iChat, and downloaded "Gay Bar" by Electric Six. Those two things would change my life, because as I listened to the song, I typed, "I want to take you to a gay bar," into my chat with The Boy. Those stupid lyrics led to us discussing gay sex, which led to a discussion about Anaïs Nin, which somehow led to a discussion about pee fetishes, which ultimately led to a discussion about how horny both of us were getting from talking about how horny we were. In a fit of sudden sexual frustration, I took my chance. "I want to fuck you," I typed. "I’m tired of being a virgin :/"

Our relationship had always been completely platonic, and he resisted. But I begged and pleaded and argued. The Boy finally acquiesced. That was how I ended up at his dorm on a Tuesday night. ("We can’t do it here," he said dubiously when I arrived. "This is the honors college. No one here fucks.")

### Illustration by Thomas Pitilli

It was pouring rain. We walked quickly to CVS, where we argued momentarily about who would buy the condoms. He pressed ten dollars into my hands and pushed me inside. I wandered my way back to the farthest aisle, eyeing the contraceptives. The variety baffled me. I picked ones in a blue box. The man in line in front of me looked to be buying all of his groceries for the whole goddamn week from CVS. He seemed to take forever as I stood in the queue with my embarrassing purchase. When he finally left, I slid the condoms gingerly onto the counter. I bolted as soon as I paid.

We wandered around West Philly in the rain, looking for a good place. There was a little alley between two fences, and it was the best we could do. It was still raining. The ground was mud. We didn’t say much. I led The Boy’s hands to finger me first, to make sure I would be wet enough to get it in. He hurt more than he helped, and we gave that up quickly. He slowly undid his jeans and opened the box of condoms. I turned to glance at him behind me, but he grabbed my head and turned it back. "Don’t look," he said. I closed my eyes. Then I was laid out on a tree stump, with my hips in the air and my hair pressed into the mud. My skirt was still on, but flipped up, and I was exposed and vulnerable beneath him. My panties were tossed somewhere in the dirt. The rain poured harder down on both of us.

###With my eyes still closed, I directed The Boy inside me. He missed at first. He squirmed around on top of me, repositioning himself. I opened one eye a little bit, to watch him. He was so beautiful. My hands reached up to his lower back, to push him into me and I slipped them gently under his sweatshirt. We were still almost entirely clothed. He was nearly inside of me, and yet we were barely touching. It seemed so dismal, I wanted badly just to kiss him. Despite everything we’d promised about not having feelings for each other, I realized I loved him. I had always loved him. He pushed in and it hurt. I whimpered, "Keep going." He pushed deeper. "Okay, now fuck me — oh. Except you just pulled out."

"I know," he said. "I came." He got off me abruptly. "Now I know," he mused. "I don’t like girls."

"Oh." I felt empty inside. I just lay for awhile on the stump in the fence-alley in West Philly staring at the sky. The rain came down on my face and my hair and my naked lower half where I still hadn’t covered myself with my skirt. Then I cried.

NEXT: "I was born and raised into a Hasidic community…"

9. "I was born and raised into a Hasidic community…"

Male • 19 years old • Brooklyn, NY

I was a month short of nineteen, and it was my wedding day. At three o’clock in the afternoon I had an appointment with the "groom instructor," a rabbi who specialized in teaching young grooms the ins and outs of sex. No pun intended.

I was born and raised into a Hasidic community where separation of the sexes was so extreme that men and women walked on different sides of the street. Sex education was not only non-existent, the mere acknowledgement of the act was enough to turn faces red. I was vaguely aware of romance as a secular (and very uncouth) form of interplay between the sexes. Pornography was a word I looked up in the dictionary years later. I knew nothing of female anatomy except that girls had no penises. I knew sex involved the male organ entering some crevice in the female body, and I imagined — perhaps just by intuiting a male-female anatomical symmetry — that said crevice was somewhere in the nether regions. Lacking anything more substantial, I spent most of my teen years imagining that point of entry to be what others considered only a point of exit. Needless to say, I had mixed feelings about the whole idea.

At exactly three p.m. I knocked on the rabbi’s door, and an emaciated-looking man with a very long beard led me into his study. Heavy religious texts were strewn about on almost every available surface.

He opened a large volume lying on the desk and read the first paragraph: "One who marries a virgin takes possession of her, and separates from her immediately." In other words, after the act, one must adhere to the applicable laws regarding a menstruating woman — the most important of which is, no physical contact whatsoever.

I freaked out. I needed the basics, not the religious laws on what comes afterwards. I needed to know what goes where, what to say to her, what or what not to wear. I wanted technical details of biology, perhaps some guidance on positions, and the like. But I was too stunned to say anything.

Throughout the session he referred to sex as "the mitzvah," literally, "the commandment," which was also the term my friends and I later used on those rare occasions we dared mention it, a topic deemed so vulgar that even with the euphemism it felt taboo.

Luckily, after twenty minutes the rabbi closed his book. "Tonight," he said, "when the wedding is over, begin preparing for the mitzvah right away, since it will be late and it must be done before daybreak."

I freaked all over again. Tonight? Given my mistaken notions of what the sexual act entailed, I wasn’t prepared for such immediacy. I needed time. I wasn’t even sure I was attracted to the girl I was marrying; as was customary, the marriage was arranged, and I’d only met her for a brief fifteen minutes prior to the engagement party six months earlier.

### Illustration by Thomas Pitilli

After this nerve-wracking hour, however, my concerns were sufficiently allayed when the rabbi explained the act with a lot of hand gesturing. It was still an entirely unexciting proposition, but I felt comfortable enough to go through with it.

Hours later, with the wedding party over, the guests gone, and the gifts inventoried, my new wife and I began preparing for the mitzvah. Dressed in the requisite clothing (nightgown for her, nightshirt for me), with a heavy sheet hung over the window curtains to ensure total darkness, we fumbled our way into bed. Still virtual strangers, we moved about each other shyly, awkwardly adjusting to the unfamiliar intimacy. I did exactly as I’d been told: I gave her a kiss on the lips, said "I love you" in Yiddish (incidentally, a language most unsuitable for amorous expression), and we both lifted our clothes as I moved on top of her.

Something was definitely wrong. A piece seemed missing. I was sufficiently erect, she claimed to have no anatomical peculiarities, but something didn’t fit. Hard as I tried, I couldn’t get my penis into any kind of body cavity.

It was almost four in the morning, but I didn’t care. I called the rabbi. "Tell her to lubricate her area with some water," he advised and hung up. We tried that. Nothing doing. I called the rabbi again. "Tell her to take your ‘organ’ with her hands and direct it to the position."

After many more tries, my penis long flaccid by the unerotic disaster the whole business had become, we determined that I must have already penetrated, and we called it a night. Owing to the intricacies of Jewish law, we couldn’t have sex for the next two weeks. After which we tried again, and pretty much the same thing happened. After another two week interval we tried it again.

Given our track record, the whole thing was turning into a drag. Expecting another frustrating round of fumbling in the dark with vague guesses as to whether it had "worked" or not, we braced ourselves and looked forward to getting it over with. But this time something was different. As soon as my erect penis put just a little pressure against her vaginal area something magical happened. Something gave way, and all I felt was the overwhelming violence of my throbbing penis, a sensation I’d never felt before.

###I can’t say my wife felt as much pleasure as I did, but she was definitely relieved to know that it finally "worked." We felt like congratulating ourselves; it was our first challenge as a married couple, and we’d pulled it off.

It would be a long time before sex would come to resemble anything like the pleasurable experience intended by nature. It took months before I dared to caress her back, touch her breasts, put my hands on her butt, and suggest we get fully naked. But when those moments came — as we navigated this new carnal territory, finding our own rhythm in the act previously considered so animalistic and therefore, best avoided — they carried an erotic energy that would be unmatched by anything later on.

NEXT: "I think about him even thirty years later…"


10. "I think about him even thirty years later…"

Female • 17 years old • Tacoma, WA

It was 1979. I think about him even thirty years later. I was a senior in high school. Jeff had graduated the year before. I had unknowingly stolen him from my best friend. He was taking a class on our extended campus. I met them at morning break, outside my class. It was an unusually warm sunny spring day for Washington. Our eyes met and the three of us sat down — him in the middle — of a loading dock. As the conversation continued he laid back in the sun. I instinctively put my hand on his stomach. He sighed.

He came to my house a few nights later with my sister’s new boyfriend — I had no idea of the friendship between the two guys and my sister. We started dating after that night, talking and smoking weed at the beach. Our foreplay lasted that whole summer. Four months worth of stolen nights in cars, on the beach, in grassy fields. He was the first man who ever told me I was beautiful. The day of my sister’s October wedding to her beau was to be our night of consummation.

### Illustration by Thomas Pitilli

My sister had left me the keys to her house. After the wedding that day, we had changed into our regular clothes. We went into their bedroom, took off our shoes but kept our flannel shirts and jeans on. We crawled under the covers and began to peel off the layers of clothing going into our usual kissing, touching, and then slowly, slowly we were naked. Jeff was not a virgin, but he knew I was because we had tried the night before without success at his house. I was tight, and he was gentle. But tonight there was no stopping what we both knew would happen.

He got on top and went into me in small, slow, easy movements. Once my body yielded it was like a whole part of me was complete. Being touched in a formerly untouched region was ecstasy. I can still remember the feeling thirty years later of the whole of my body connected with his. His gentle stroke, our eyes together, kissing fully. It was fantastic. After, we stole strawberry ice cream from their freezer and ate it out of the half-gallon carton, sharing one spoon while he fed me. Laughing because we had moved the bed off its frame.

###We stayed together for three years. We made love everywhere. In cars, a boat, movie theatres, a forest. We broke up when I moved to San Francisco. He came to try to get me to move home. We made love every night for the three weeks he was there. I decided to stay, opting for the city life I always had craved. I can still see him on the San Francisco Airport’s rooftop parking lot, walking across the empty parking spaces after our last talk.

We would go on to be married for fourteen years, and eventually moved on to have sex like pretty much everyone else. But the innocence of those early days and weeks is still something to be remembered.

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