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 Hooksexup-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..."