Some fantastic educational books on sex have been published in the last few years, and the following attempts to summarize (by topic) a selection of what is currently in print.
One very popular choice right now is the latest edition of the lighthearted yet comprehensive Guide to Getting It On!, and another is the venerable The Good Vibrations Guide to Sex (which covers sex toys particularly well). Both are well-written and illustrated, and would be good places to start learning.
If you primarily have sex with women, and aren't really interested in hearing about anything else, then you might consider She Comes First: The Thinking Man's Guide to Pleasuring a Woman if you're male or The Whole Lesbian Sex Book if you're female. In either case, The Smart Girl's Guide to the G-Spot would also be a smart choice.
If you primarily have sex with men, and aren't really interested in hearing about anything else, then you might consider Sex Tips for Straight Women from a Gay Man if you're female or 101 Gay Sex Secrets Revealed if you're male.
Dr. Betty Dodson's Sex for One: the Joy of Selfloving remains an excellent choice.
ESO: How You and Your Lover Can Give Each Other Hours of Extended Sexual Orgasm, The Multi-Orgasmic Man: Sexual Secrets Every Man Should Know [summary], and The Multi-Orgasmic Couple are all good choices.
Books about going down on women include The Ultimate Guide to Cunnilingus and The Low Down on Going Down: How to Give Her Mind-Blowing Oral Sex. Books about going down on men include The Ultimate Guide to Fellatio and Blow Him Away: How to Give Him Mind-Blowing Oral Sex.
One of the most popular books on this topic (and there are many to choose from) is The New Sensual Massage.
The classic choice is Dr. Jack Morin's Anal Pleasure and Health: A Guide for Men, Women, and Couples. Other excellent choices include The Ultimate Guide to Anal Sex for Men and The Ultimate Guide to Anal Sex for Women [review].
As a first choice we recommend Carol Queen's Exhibitionism for the Shy: Show Off, Dress Up, and Talk Hot. Other good choices include Phone Sex: Aural Thrills and Oral Skills, Sex Talk: Uncensored Exercises for Exploring What Really Turns You On, The Fine Art of Erotic Talk: How To Entice, Excite, and Enchant Your Lover with Words, and Talk Sexy to the One You Love.
Today, most of the new offerings on this subject come out in DVD rather than book format: the best of what remains in print is probably The S-Factor.
Sex Toys 101: A Playfully Uninhibited Guide is a great place to start, though if your main interest is learning to use strap-on dildos you'll probably also want to pick up a copy of The Adventurous Couple's Guide to Strap-On Sex.
You'll want to start with a general book covering the how-to and safety basics. Sensuous Magic: A Guide to S/M for Adventurous Couples is one of the best written, Screw the Roses, Send Me the Thorns: The Romance and Sexual Sorcery of Sadomasochism is one of the best illustrated, and The New Bottoming Book / The New Topping Book do a particularly admirable job covering the psychology of BDSM play (e.g. why it can be fun).
Other top-notch general books on BDSM include Consensual Sadomasochism: How to Talk About It and How to Do It Safely (co-written by a psychotherapist and very well-written) and SM 101: A Realistic Introduction (particularly thorough on safety matters).
Once you understand the basics, the following books delve into specific topics in a little more depth:
A Hand in the Bush: The Fine Art of Vaginal Fisting covers vaginal fisting, while Fist Hand: An Erotic Guide to Fisting and Trust, the Hand Book: A Guide to the Sensual and Spiritual Art of Handballing cover anal fisting.
The Art of Sexual Ecstasy: The Path of Sacred Sexuality for Western Lovers [review] is the classic choice for those who want a Western interpretation of Tantra, though Tantra Between the Sheets: The Easy and Fun Guide to Mind-Blowing Sex and The Complete Idiot's Guide to Tantric Sex are more direct and easier reads.
The Erotic Mind: Unlocking the Inner Sources of Passion and Fulfillment is a good place to start: it guides you through reflecting on your best sexual experiences, with the intent of helping you better-understand what you want and like.
The classic Exhibitionism for the Shy has some great advice on the subject of feeling sexy at any size or age, as does Big Big Love [review] (which focuses more on feelings about body weight).
The RoMANtic's Guide: Hundreds of Creative Tips for a Lifetime of Love contains a lifetime's worth of romantic ideas that your partner might appreciate.
The Lifestyle: A Look at the Erotic Rites of Swingers is the best choice to understand the history and culture of swinging. If you intend to participate, either Considering Swinging or Swinging for Beginners: An Introduction to the Lifestyle would be a better choices. On the other hand, if you're an experienced participant in the swing community and would like to start hosting swing events of your own, then Together Sex: The Playful Couple's Key to Better Sex Parties is probably what you want.
We recommend Opening Up: A Guide to Creating and Sustaining Open Relationships by Tristan Taormino as a starting point. From there, good choices include The Ethical Slut: A Practical Guide to Polyamory, Open Relationships, and Other Adventures (particularly strong on open relationships) and Love in Abundance: A Counselor's Advice on Open Relationships (particularly strong on practical communication skills).
If things get to the point where you're talking about living together, then you'll want to pick up a copy of either Living Together: A Legal Guide for Unmarried Couples or Unmarried to Each Other: The Essential Guide to Living Together as an Unmarried Couple and adapt what you read to your specific situation.
Possibilities include The Ethical Slut: A Practical Guide to Polyamory, Open Relationships, and Other Adventures (focusing on alternative relationships and polyamory) and Sex Disasters and How to Survive Them (for when something really unforseen happens).
Human Sexuality Today is probably the best "Sexuality 101" college textbook, while The Cartoon Guide to Sex is a great non-academic alternative. Woman: An Intimate Geography also deserves special mention for the fantastic job it does shedding light on the "why" of anatomy.
For practical information on reproductive physiology and health, see Dick: A User's Guide if you're male and The V Book: A Doctor's Guide to Complete Vulvovaginal Health if you're female. For information on sex and disability, see The Ultimate Guide to Sex and Disability. For information on recovering from childhood sexual abuse, see Healing Sex.
Sexy Mamas: Keeping Your Sex Life Alive While Raising Kids covers the oft-neglected subject of maintaining one's sex life after becoming a parent.
If you want to write erotica, then start with How to Write a Dirty Story: Reading, Writing, and Publishing Erotica and graduate to The Erotic Writer's Market Guide once you're ready to submit to publishers.
We were very impressed with the anthology Best Sex Writing.
Often opinionated, rarely boring, you might try any or all of the following: Wild Side Sex: The Book of Kink, Leatherfolk (leather community history), Sex Tips and Tales from Women Who Dare, and Deviant Desires: Incredibly Strange Sex (a remarkable book which takes some very unusual fetishes and makes a sincere effort to understand both the fetish as well as the community supporting it).
For ideas on long-term relationships, Keeping Mr. Right: The Gay Man's Guide to Lasting Relationships is a solid choice. For a variety of perspectives on the sex clubs and baths, try Policing Public Sex or Gay Bathhouses and Public Health Policy.
The following present several perspectives on lesbian relationships and dating: Is It a Date or Just Coffee? The Gay Girl's Guide to Dating, Sex, and Romance and The Lesbian Polyamory Reader: Open Relationships, Non-Monogamy, and Casual Sex.
Bisexuality and the Eroticism of Everyday Life is probably the best place to start, perhaps accompanied by Bi Any Other Name: Bisexual People Speak Out. For a sociological perspective, see Dual Attraction: Understanding Bisexuality.
To help sort out your own perspective on gender, My Gender Workbook may be a good place to start. If you're trying to come to grips with the gender transition of a friend or family member, then True Selves: Understanding Transsexualism - For Families, Friends, Coworkers, and Helping Professionals is what you want. If you want to gain a better understanding understanding of trans community politics and modern theories about gender, then give Queer Theory, Gender Theory: An Instant Primer a try. If you need to understand the medical community's perspective on transgender, then try Gender Loving Care: A Guide to Counseling Gender-Variant Clients and Transgender Care: Recommended Guidelines, Practical Information, and Personal Accounts.
On the other hand, if all you want to do is dress up like the opposite sex and don't identify with all this "trans" talk and gender theory, then the book The Lazy Crossdresser is probably more what you're looking for (certainly no offense is intended - that's just the title of the book).
Outing Yourself: How to Come Out as Lesbian or Gay to Your Family, Friends, and Coworkers is a terrific choice. From the other side, the book Always My Child: A Parent's Guide to Understanding Your Gay, Lesbian, Bisexual, Transgendered or Questioning Son or Daughter is very well done.
See Why You Should Give A Damn About Gay Marriage for the theory and Making it Legal: A Guide to Same-Sex Marriage, Domestic Partnerships, and Civil Unions for the practice.
To learn the basics of citizen participation in the legislative process, pick up a copy of The One-Hour Activist: The 15 Most Powerful Actions You Can Take to Fight for the Issues and Candidates You Care About. If all you want is to make a difference as an individual, that's probably the only book you need.
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