This is an interesting question because it delves with the issue of what many people would consider 'abnormal' sexuality. Specifically, penetration in this case is not just vaginal but also implies oral or anal sex. Would this invalidate a woman's status as a 'betulah' - a virgin - if she never had vaginal sex but only oral or anal sex. Without trying to sound flippant, Bill Clinton would say 'no' and he would technically be correct.
Our Sages seemt to define sex as vaginal intercourse. I know of no source that speaks of anal sex or oral sex (although there are modern commentators and poskim [Isserles] who teach that a man is permitted to kiss any part of his wife's body and vice versa. Surely that is an indication of oral sex. But that is not technically sex).The indicator that the Rabbis used to define a woman's status for marriage was someone whose hymen was intact. Indeed, someone was a virgin if they had a hymen and, if they didn't for whatever reason such as an accident or birth defect and wanted to marry as a virgin, she would have to go to the Beit Din with her father (usually) who would testify to her virginity in a variety of ways. There was no way to know if a woman had anal sex or oral sex in the past (provided it was not a frequent sexual practice). Sex seems to be defined as vaginal sex. Indeed, our Sages forbad unmarried men and women (but most women) to be alone together for fear that sexual intercourse would take place for such would constitute a marriage (see Mishnah Kiddushin 1:1).
So, technically, sex is vaginal when a man makes penetration. From a legal point of view, that should not change the status of the ketubah. From an intended point of view, though, it is a bit more problematic.
The Rabbis were, for lack of a better word, prudes. They liked women to be pure, angelic, untouched, flowered, etc. Anything that disturbed a woman's purity was, for the Rabbis, something that affected their 'worth' - literally and figuratively. So if they engaged in any kind of behaviour that sullied themselves, their bodies, or their reputations, that would make their worth diminish. It is possible that they would consider pre-marital oral or anal sex which involved penetration to be on the 'this is sex' list. I must admit that it is a remote possibility, though, since the definition of sex by our Sages is much simpler.
The Ketubah, or marriage document, is – to borrow from current technology – content sensitive. That is to say, while the amounts (for weddings outside Israel) standardized are vestigial, the document still requires precise information for the date, the location, the names of the bride and groom, and the bride’s marital status. Rabbis are responsible for ensuring that before they officiate at a wedding ceremony, the information on the document is accurate. The traditional categories for the bride’s marital status are betulta, giyorta, and armalata: Aramaic for a woman previously unmarried, previously married and divorced, and previously married and widowed respectively. The standardized monetary values assigned to each category (and the wording in the Ketubah) will vary according to her status.
Some confusion lies in the fact that the word “betulta” is usually translated as “virgin.” Hence, if the bride had been sexually active before the wedding – depending upon what sexually active means - some would imagine that this would remove her from the category of “betulta.” But this is not the case. Betulta is not, for the purpose of the Ketubah, an attestation of the bride’s virginity but, rather, an affirmation that she had not been previously married. Her sexual history is not taken into consideration.
There is an interesting response once given by Rabbi Moshe Feinstein to a young woman who led a promiscuous life before she turned religiously observant. She wanted to know whether she had to reveal her history to her fiancé. Rabbi Feinstein ruled that she was under no obligation to report her past, but if asked, she may not deny it. He had no qualms about the validity of a Ketubah that would describe her as a “betulta” even though she was not a virgin.
I understand that sexuality is a very touchy subject, so I will try to show my utmost sensitivity. On the other hand, I don’t do sugarcoating so I will take a straightforward approach to the question.
Judaism is very real about how people react to sexuality. They were aware of people’s preferences both in the bedroom and in what they look for in a relationship in general, regardless of whether those desires are shallow. At the same time, the sex act is considered to be the holiest act that a person can engage in, when done in a holy way: the right times with the right conduct and of course only with one’s spouse. Sex is literally the way to become G-dly by participating in the very act of creation itself. It is the balance of these two considerations that generates Jewish law and thought on the issue.
The Rabbis recognized that guys highly prize virginity, and purity in general. This is even to the point of hypocrisy. It is for this reason that a woman who is a virgin receives a larger sum written into her ketubah (pre-nuptial agreement) than does a widow or divorcee. The Gemara in Ketubot even entertains the possibility that a woman loses her rights to the extra money if her hymen was broken by an object since there already be a loss of grace in the eyes of the men, who are the ones obligated to pay the sum stated in the ketubah in the event of death or divorce. Yes, guys do think this way and care this much. The following story from the Gemara in Ketubot illustrates:
A newly-wedded man came to complain to Rav Nahman the night after his first night with his new wife that she wasn’t a virgin. He complained that she was too loose to have been a virgin. Rav Nahman flogged him because there’s no way that a bachelor could have known if she was loose or not unless he had been promiscuous beforehand.
The Rabbis equally recognized that women have less of a hangup, and that their primary concern is the relationship. They very much want to be in a relationship, even if the guy isn’t particularly quality. The Rabbis tell us that a woman would rather be married to someone that is gross rather than be considered a whore. Even in these times where hook-ups and living together are common I see women feel this way. I remember a female friend of mine in high school who had very little connection to religion dumped a guy after he said there was nothing to their relationship except sex.
Biblically speaking, the only acts that actually change a woman’s status, and that would incur some kind of legal action in court for both partners, are sexual intercourse and “unnatural sex”. They both render a girl legally a non-virgin with some odd quirks if the couple were to only engage in “unnatural sex” before a girl were to lose her virginity under the normal understanding of the term. A girl who did everything but these two activities would be a virgin. That doesn’t mean that philosophically speaking it’s okay, just that it wouldn’t be a fact a girl would necessarily need to share with a guy if they know the guy will flip because it doesn’t have any legal ramifications anyway.
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