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I wanted to post an answer earlier but I figured I should check Otzar HaPoskim first. Unfortunately HebrewBooks only had volume one. So over Shabbos I popped into a shul that has the set. There was nothing there. Not even a mention of the B.Sh. and Ch.M. that @sam mentions in his answer. Very surprising. But I digress. Here's my thoughts. Once upon a time I ...


This topic is largely treated in Talmudic books. We are going to start with a Mishna in Sanhedrin 9, 6 וְהַבּוֹעֵל אֲרַמִּית, קַנָּאִין פּוֹגְעִין בּוֹ .‏ Or cohabits with a heathen [lit. syrian {Aramean}] woman, he is punished by zealots. One see that in some circumstances, not treated in this post, man involved in intimate relation with a ...


I don't know if this is lechalach, especially since it expresses both as very bad in different ways, but the tanya certainly describes this at the end of chapter 7: He explains that zera levatala is in one regard worse, because quantitatively, a person who sins such brings many more klipot ("bad forces") into the word than by forbidden relations. ...


There is a machlokess between the Tur and the Rambam if it is permissible to have relations with a non Jewish woman in a pikuach nephesh situation. See Hitler Youth Solomon for a case where this occurred. It sounds like this person's rabbi is trying to fill him up with sexual guilt about masturbation.


Probably wasting seed [NOT deliberately], because there, if it comes out against his will, so he is an ones. As opposed to deliberately doing something that is forbidden.


The Gemara Pesachim 113a says אמר רבי יוחנן שלשה מנוחלי העוה"ב אלו הן הדר בא"י והמגדל בניו לתלמוד תורה והמבדיל על היין במוצאי שבתות מאי היא דמשייר מקידושא לאבדלתא And the Rashbam writes: דמשייר מקידושא. שיש לו מעט יין ומונע שתייתו בשביל הבדלה Rabbi Yochanan said that if saves what little wine he has for Havdalah, he inherits the world-to-come. ...

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