A Commentary, Critical, Practical, and Explanatory on the Old and New Testaments, by Robert Jamieson, A.R. Fausset and David Brown  at sacred-texts.com
pro 5:1A warning against the seductive arts of wicked women, enforced by considering the advantages of chastity, and the miserable end of the wicked. (Pro. 5:1-23)
This connection of wisdom and understanding is frequent (Pro 2:2; Pro 3:7); the first denotes the use of wise means for wise ends; the other, the exercise of a proper discrimination in their discovery.
pro 5:2regard--or, "observe."
pro 5:3(Compare Pro 2:16). Her enticing promises are deceitful.
pro 5:4her end--literally, "her future," in sense of reward, what follows (compare Psa 37:37; Psa 73:17). Its nature is evinced by the use of figures, opposite those of Pro 5:3. The physical and moral suffering of the deluded profligate are notoriously terrible.
pro 5:5feet . . . , steps--that is, course of life ends in death.
pro 5:6her ways . . . know--Some prefer, "that she may not ponder the path of life," &c.; but perhaps a better sense is, "her ways are varied, so as to prevent your knowledge of her true character, and so of true happiness."
pro 5:8Avoid the slightest temptation.
pro 5:9thine honour--in whatever consisting, strength (Pro 3:13) or wealth.
thy years--by cutting them off in dissipation.
unto the cruel--for such the sensual are apt to become.
pro 5:10wealth--literally, "strength," or the result of it.
labours--the fruit of thy painful exertions (Psa 127:2). There may be a reference to slavery, a commuted punishment for death due the adulterer (Deu 22:22).
pro 5:11at the last--the end, or reward (compare Pro 5:4).
mourn--roar in pain.
flesh and . . . body--the whole person under incurable disease.
pro 5:12The ruined sinner vainly laments his neglect of warning and his sad fate in being brought to public disgrace.
pro 5:14evil--for affliction, as in Gen 19:20; Gen 49:15.
pro 5:15By figures, in which well, cistern, and fountain [Pro 5:15, Pro 5:18] represent the wife, and rivers of waters [Pro 5:16] the children, men are exhorted to constancy and satisfaction in lawful conjugal enjoyments. In Pro 5:16, fountains (in the plural) rather denote the produce or waters of a spring, literally, "what is from a spring," and corresponds with "rivers of waters."
pro 5:17only thine own--harlots' children have no known father.
pro 5:18wife . . . youth--married in youth.
pro 5:19loving . . . roe--other figures for a wife from the well-known beauty of these animals.
breasts--(Compare Sol 1:13; Eze 23:3, Eze 23:8).
ravished--literally, "intoxicated," that is, fully satisfied.
pro 5:21The reason, God's eye is on you,
pro 5:22and He will cause sin to bring its punishment.
pro 5:23without instruction--literally, "in want of instruction," having refused it (compare Job 13:18; Heb 11:24).
go astray--literally, "be drunken." The word "ravished" (Pro 5:19) here denotes fulness of punishment.