Concise Bible Dictionary:

Used symbolically for the seat of deep affection. John speaks of the Lord Jesus as the only begotten Son “in the bosom of the Father” (John 1:1818No man hath seen God at any time; the only begotten Son, which is in the bosom of the Father, he hath declared him. (John 1:18)). The tender and sacred relationship which husband and wife have to each other is also called the “bosom” (Deut. 28:54, 5654So that the man that is tender among you, and very delicate, his eye shall be evil toward his brother, and toward the wife of his bosom, and toward the remnant of his children which he shall leave: (Deuteronomy 28:54)
56The tender and delicate woman among you, which would not adventure to set the sole of her foot upon the ground for delicateness and tenderness, her eye shall be evil toward the husband of her bosom, and toward her son, and toward her daughter, (Deuteronomy 28:56)
). This to an Israelite would give force to the description of Lazarus being carried into ABRAHAM’S Bosom (Luke 16:22-2322And it came to pass, that the beggar died, and was carried by the angels into Abraham's bosom: the rich man also died, and was buried; 23And in hell he lift up his eyes, being in torments, and seeth Abraham afar off, and Lazarus in his bosom. (Luke 16:22‑23)). By means of a loose garment and a girdle, many things are constantly carried by Orientals in the bosom, even such as a lamb (Isa. 40:1111He shall feed his flock like a shepherd: he shall gather the lambs with his arm, and carry them in his bosom, and shall gently lead those that are with young. (Isaiah 40:11): Compare Luke 6:3838Give, and it shall be given unto you; good measure, pressed down, and shaken together, and running over, shall men give into your bosom. For with the same measure that ye mete withal it shall be measured to you again. (Luke 6:38)).

From Manners and Customs of the Bible:

The term “bosom” frequently refers, in Oriental usage, to the folds of the garment as they extend beyond and droop over the girdle. This part of the dress is also called the “lap.”‘ See 2 Kings 4:3939And one went out into the field to gather herbs, and found a wild vine, and gathered thereof wild gourds his lap full, and came and shred them into the pot of pottage: for they knew them not. (2 Kings 4:39), and see also note on Neh. 5:1313Also I shook my lap, and said, So God shake out every man from his house, and from his labor, that performeth not this promise, even thus be he shaken out, and emptied. And all the congregation said, Amen, and praised the Lord. And the people did according to this promise. (Nehemiah 5:13) (#380). It is used as a receptacle for various articles, as pockets are used with us; though some things are deposited there which we would not put into our pockets. Fathers sometimes carried their children here. See Numbers 11:1212Have I conceived all this people? have I begotten them, that thou shouldest say unto me, Carry them in thy bosom, as a nursing father beareth the sucking child, unto the land which thou swarest unto their fathers? (Numbers 11:12) and note on Isaiah 49:2222Thus saith the Lord God, Behold, I will lift up mine hand to the Gentiles, and set up my standard to the people: and they shall bring thy sons in their arms, and thy daughters shall be carried upon their shoulders. (Isaiah 49:22) (#522). Here also the shepherd carried the lambs. See 2 Sam 12:3; Isaiah 40:1111He shall feed his flock like a shepherd: he shall gather the lambs with his arm, and carry them in his bosom, and shall gently lead those that are with young. (Isaiah 40:11). To this custom of making a receptacle of the folds of the dress there are frequent allusions. See Job 31:3333If I covered my transgressions as Adam, by hiding mine iniquity in my bosom: (Job 31:33); Psalm 79:12; 89:50; 129:712And render unto our neighbors sevenfold into their bosom their reproach, wherewith they have reproached thee, O Lord. (Psalm 79:12)
50Remember, Lord, the reproach of thy servants; how I do bear in my bosom the reproach of all the mighty people; (Psalm 89:50)
7Wherewith the mower filleth not his hand; nor he that bindeth sheaves his bosom. (Psalm 129:7)
; Proverbs 6:27; 17:23; 21:1427Can a man take fire in his bosom, and his clothes not be burned? (Proverbs 6:27)
23A wicked man taketh a gift out of the bosom to pervert the ways of judgment. (Proverbs 17:23)
14A gift in secret pacifieth anger: and a reward in the bosom strong wrath. (Proverbs 21:14)
; Isaiah 65:66Behold, it is written before me: I will not keep silence, but will recompense, even recompense into their bosom, (Isaiah 65:6).
This is the custom referred to in the text; though we are not authorized to infer, as some have strangely done, that grain and other articles that are measured in the way suggested in the text were literally carried in the bosom. The figure is double, and the design is to express the reflex benefits of good deeds; they will come back in full measure to bless the giver.

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