Buckle up guys and gals, here is a pretty wild teshuva from the Dembitzner Rov regarding anal sex. (For more about the Dembitzner Rov, check out https://mishpacha.com/49th-st-hub-of-halachah/ ) Here is my loose translation:
Question: During the month of Kislev, 1965, I received a question regarding anal sex, and I have been too discombobulated to answer. A young man approached me with tears in his eyes and related to me the following story. His wife was suffering from a condition in her vagina that, according to the doctors, prevents them from having intercourse for the next eight or nine months. The woman continued going to the mikvah as usual in order to be allowed to hug and kiss her husband. However, all the physical contact with his wife was causing the husband to have evil thoughts, leading to him purposefully making his penis hard and even leading to actual masturbation.
The wife has agreed to allow him to have anal sex with her until her illness passes. However, aside from his general disgust at doing such an act, the husband is too terrified of sin to do such an act. As an aside, the doctors believe that it is medically fine to do such a thing in this case. Now, this young man is coming to me crying, seeking advice on how to proceed. I requested that he find another Rov to ask since I am too scared to issue a pisak on this matter. However, he will not leave me, and he returns every day to me. Eventually, I could no longer see his distress, and I thought to myself that perhaps there is a way to allow such an act.
[The teshuva goes through some of the previous authorities discussing anal sex and the terrible sin of masturbation]
Answer: ...Therefore, I said to the man that if he sees in himself that if he is deprived of anal sex, he will end up masturbating, he would be allowed to have anal sex, as long as it was in an infrequent manner. However, I told the man that he must distance himself from further kissing or hugging his wife for the remainder of her illness in order that he no longer become aroused and be forced to either masturbate or have anal sex. I also told him that Heaven forbid should he have anal sex simply for enjoyment. His permission was only if he was in such a state that the alternative would be committing the sin of masturbation.
I also told the man that I was only going to allow this act if he asked two other rabbonim, and they agreed with me. I also told him that he and his wife must take a strict vow that as soon as the illness was over and they could have vaginal intercourse, they would never again for the rest of their lives engage in anal sex. (This is necessary in order to demonstrate that the heter I was giving them was only because the situation was under incredible duress.)
Furthermore, after each act of intercourse, they should set aside money for charity to recognize the unfortunate fact that they are forced to do this act like an animal. (See the Aizer Mikdash for further restrictions. However, it is possible that we do not need to be so stringent.)
After all that, I changed my mind; I did not want to be the first Rov to ever allow anal sex. Perhaps once I allow this couple to engage in anal sex, they will become accustomed to this form of intercourse and, once entrenched in sin, they will be unable to resist the temptation to continue having anal sex. Therefore I told the man that he must first ask other rabbonim. Only once he finds two rabbonim that allow him to have anal sex would I co-sign as the third voice of support. However, I am simply unable to accept being the first to give the heter, even if he finds two other people to co-sign with me.
After this, I told the man that I would speak to his wife on the telephone and convince her to stop going to the mikvah and to ask that she no longer request that her husband hug or kiss her. Through this plan, the husband will not come to bad thoughts or masturbation, nor would he end up forced to do this animalistic act [anal sex], which is a great sin according to many great sages. With the help of God, this plan worked, and I did not need to deploy any sort of heter in this matter, and I give thanks to Hashem that I did not need to stick my head between the teeth of the lions. Blessed is the Savior and Redeemer.
Kislev, 1965
Brooklyn
Ok. That was an emotional roller coaster. Do you think he gave the couple wise and correct guidance? If you disagree and think he is just some whack job who doesn’t represent actual Jewish thought, remember that according to Mishpacha “…he was one of the foremost poskim of the last generation and provided shimush (rabbinical internship) for a vast number of American rabbinical students of his time no matter their affiliation” and that “Dayanim and rabbanim worldwide give much weight to his halachic rulings and consider his Be’er Moshe — an eight-volume set of responsa which he began compiling in 1969 — an essential part of their library.”
The teshuvah prior to this one spends several pages discussing whether a man is allowed to insert his fingers in a woman's vagina. I am sure it is going to get crazy. Stay tuned. I will read it over Rosh Hashana and post it here.