My First Time

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.

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.

We're looking for stories about the first time you had sex. Email with 500-1000 words. (Don't worry, we won't print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.
According to just about every pre-college advice manual, floorcest is a bad idea.
"So no, I didn't lose my virginity in the most traditional way."
"He looked like if Ian Somerhalder and Gerard Butler had somehow created a baby."

Commentarium (44 Comments)

Feb 16 10 - 2:20pm

Wow! Fascinating. More like this, please.

Feb 16 10 - 3:41pm

This was thought provoking, excellent reading. Thank you for this.

Feb 16 10 - 4:36pm

fascinating indeed. so i guess after fourteen years they separated eh?

Feb 16 10 - 4:42pm

I guess a lot of Hassids blog here.

Feb 16 10 - 5:44pm

Interesting, but in a very clinical sense.

Feb 16 10 - 6:52pm

This was terrific, I've never heard an account of this before, very compelling.

Feb 16 10 - 6:58pm

I would love to hear the wife's account of this!

Feb 16 10 - 11:55pm

Nice story, except for the part that... the bride/wife in this story resembles the blow-out toy from Ricky's!

Feb 17 10 - 10:24am

God, this is so depressing. the more i hear about any religion poking (or in this case, not poking in enough) into our sex lives the more i'm turned off by all religion completely. This poor poor man! and damn, his poor wife!

Aug 16 12 - 6:31pm

Maybe you missed the part about being happily married 14 years later. Sure, it was awkward, but I wouldn't pity them.

Feb 17 10 - 11:04am

This is by far the most interesting one of these I've read. Most of them are pretty trite and boring but this was really fascinating. I know some Hassids but most of them had sex prior to marriage (although I realize they don't talk about it).

Feb 17 10 - 11:19am

Did it never occur to him (or her) to do some research on his/her own? It's not like there was a shortage of publicly available info at any bookstore, even way back then (I'm supposing this was before the web.)

Feb 18 10 - 1:53am

What is a shiksa?

Feb 18 10 - 2:41am

next time call me I'll get her warmed up for ya

Feb 18 10 - 11:26am

a good reason to get married at 14.

Feb 19 10 - 1:21am

I agree with earlier comment by AMF... perhaps to an even less tolerant degree. Bombarded by such grotesquely primitive mores, cultural divisions I feel perpetually grouchy and critical about what people think is "meaningful" in this life.

On the part of its advocates religion is used to be divisive, manipulative, confounding, and intellectually suppresive. This is intensely irritating to me (something I love to hate - truly). On the part of its followers, religion is pure idiocy - providing ignorant comfort, an inability to think critically, and cultural separation - based on supremely inconsistent systems of belief. Gross.

Feb 18 10 - 4:16pm

Really interesting story! Opened my eyes to the different perspectives of cultural upbringing. In the UK we have compulsory sex-ed and my parents were very open about the topic of sex. Great story :)

Feb 18 10 - 5:35pm

I very much agree with KG. What disgusting repression, reminiscent of the middle east. When I was young, in the 70s, we read up, we got protection, we made love with the lights on, we lived together "without benefit of marriage," our parents were convinced that the world was going to hell in a handbasket, and everything turned out fine.

Feb 18 10 - 10:01pm

That is the most pathetic story I ever heard!

Feb 18 10 - 10:36pm

I'm a gay guy and I was able to get it up and into a woman faster than this. It isn't rocket science.

Feb 19 10 - 12:27am

Word, RL.

Feb 19 10 - 4:17pm

Great, sex for godly people is quite scary. haha
but i hear that Jewish people have very "fullfilling" sex lives. more than can be said for me (-.-)

Feb 21 10 - 11:41am

Savages. Well, at least they wised up and moved on--even if it took them 14 years.

Feb 22 10 - 11:58pm

Why is it so hard for people to believe that this kind of stuff really happens?

Feb 23 10 - 9:46am

I'm dismayed so many take this as a negative view on religion. It's their right to take whatever view to sex they feel appropriate. If it works for them, it works for them. Why should everyone be the same?

I thought this story was quite enchanting.

Feb 24 10 - 12:07am

Reminds me of Adam and Eve, awakened to the world through sexuality. Beautiful.

Feb 25 10 - 6:41pm


It's not about the sex - or the way that people have sex. If this is how you (the royal "you") "get down", then great. But I didn't gather from reading this that this was that couple's fettish. It seems obvious (to me) that it was not optional but obligatory.

The problem that I, for one, have with this is closely connected to my view that religion, culture, politics, and rhetoric continue to be used as divisive instruments, brands even. Endless conflict derives from all of this dogma. Endless - it seeps into economics, policy, attitudes, prejudices, conspiracies etc.

It illustrates to me that:

1. we are as yet quite primitive, tribal even


2. there are intrinsic limits as to how cohesive we can be as people (across cultures) - confirming #1, essentially.

Because as long as religion exists, then so does (I believe) humanity's most effective form of manipulative, divisive rhetorical device. To make it worse, logical and scientific evidence do not support the world's common religious views. [Isn't it quite convenient that in order to believe, I have to set aside all forms of logically consistent evidence.] That is to say, we're producing all of this social tumult for a pile of ideological inconsistent nothingness.

Aug 16 12 - 9:15pm

So your theory is that with no religion there would be no more conflict? Wow, it's amazing to see such naivete. Try to remember something, for every bad thing you saw done in the name of religion there were probably 100 good things done in the name of religion...they just don't make the news.

Feb 25 10 - 6:58pm

Everyone has the right to their culture and religion, even the Jews. The criticism of religion here is on par with criticizing other stories for violating scripture. Anyone who wants to eliminate religion can leave some flowers by Stalin's grave.

Feb 26 10 - 1:32pm

Thank you for sharing your story. :)

Mar 05 10 - 5:54am

@RL...i love how you completely gloss over the negative aspects of the 'free loving '70s' like say the fact that things like AIDS flourished in part because of such a casual attitude towards sex. Also, I think that many people would take issue with the assertion that 'everything turned out fine.' shit happens and you can't just simplify it down to 'religion=bad,' my way of life=good. There are a lot of highly religious people out there who have more consistently pleasurable sex lives and I'm sure that there's plenty of people with beliefs like your who don't.

Mar 17 10 - 12:21am

I think this ended up being a beautiful story of two people who, albeit awkwardly, grew closer through their process of learning about sex together; discovering their own and each other's bodies, exploring new carnal territory and their own rhythm....sounds like good sex to me. And fourteen years is not a bad run, is it? If most of those years were good, well was a good life together. I too would like to hear this story from the wife's point of view (I'm a guy).

Mar 30 10 - 6:44pm

@S: Who said anything about "free loving?" I married the person to whom I "lost" my virginity. Our circle of friends weren't promiscuous, but everyone had a lover. They've all become highly ethical, contributing members of society, mostly with better-than-average, equal, and intellectually stimulating marriages. My point was that we weren't hobbled by medieval guilt trips and lack of knowledge about sex and the human body. The writer describes his complete cluelessness about such things, at 19. That is willful ignorance, these days especially. He may be willing to entrust such knowledge to "an emaciated-looking [rabbi] with a very long beard." I wasn't. And yea these many years later, I can say to those younger people among whom I once counted myself, "I was right."

Apr 24 10 - 4:02pm

RL whats so right about being right?

Apr 24 10 - 4:03pm

Lets wipe out the morally inferior religionists!

Jul 03 10 - 6:52pm

I loved this story and very brave of you to write it. My family is Orthodox Jewish but not me. I dated an ex-chasidic guy who had a similar story. It's a much different world and I'm not here to judge any religion. Mazel Tov for telling this story.

Aug 31 10 - 2:27pm

Having come from a Muslim background, I'd heard whispered stories from female cousins, and those who swore, after the first night, that they NEVER would again. I've wondered what it was like for the guys - I knew some of my male cousins messed around, but in most cultures, I wondered: do they get complete freedom to mess around and learn? Does daddy hire one of the prostitutes he spits at in public, but uses in private? Or is it similarly shrouded? In these cultures, women just have to 'take it' - but the men have to 'give it' - how do they learn? I loved your story - beautifully written, heartachingly honest. Thank you and mazal tov on having the courage to do so.

Aug 31 10 - 2:27pm

Gah, that should have been 'thank you for sharing and mazal...' xx

Oct 01 10 - 8:24pm

Yes, sure, I like it, Interesting and educational. Please continue to write more interesting post in your website.

Feb 04 11 - 11:23pm
Download Amiya

Man, you wrote a long post.

Feb 18 11 - 1:02am

nice pictures, good!

Feb 18 11 - 9:42am
Keygen Tessa

Whay are you don't publish actual news?

Jan 25 12 - 7:43am

I am also an Orthodox Jew and I am quite surprised by how inadequately you were prepared. I lived with a similar amount of segregation of genders, the only difference was, however, that prior to marriage I was much better prepared. First of all, instead of the day before the wedding, we were summonded to go to "class" ,the groom with the rabbi, the bride with his wife for several weeks. We discussed relationships, how to relate to the opposite gender, and Jewish laws on marriage and sex. We were given practical advice without any embarrassment or awkwardness. . I am surprised that things were done the way that they were in this case.

May 15 12 - 1:27pm

Cool story. I always wondered about the practicalities of having sex after such segregation: traditional Christian cultures were the same at least in their ideals of complete asexuality before and outside of marriage, and I count myself as a traditional Christian. It's a sublime ideal to my mind, but I always thought it was terribly impractical, since at least in my experience as a man, you definitely need a fair amount of practice to get good at it (I really relate to the part about not finding the cavity!). But the story shows that it can be all right to practice with your own spouse: having an awkward first night doesn't have to ruin the whole marriage. It's also amusing to see this man approaching the act as such a burdensome obligation! Unfortunately like many guys I was cursed with perverted fantasies about sex, and I kind of like this man's attitude, which keeps sex in a subordinate place, not letting it take over his entire mind.