1 Introduction

1.1 What We'll Be Covering

1.2 What We'll Leave to the Professionals

1.2.1 STD Differential Diagnosis

1.2.2 Pros and Cons of Specific Birth Control Methods

1.2.3 Sexual Side Effects of Specific Prescription Medications

1.2.4 ``Edge Play''

1.3 Why I Wrote This

2 Sex

2.1 How the Body Works

2.1.1 Sexual Anatomy

2.1.1.1 What's What

2.1.1.1.1 On Females

2.1.1.1.1.1 External Anatomy

2.1.1.1.1.2 Vaginal Anatomy

2.1.1.1.2 On Males

2.1.1.1.2.1 The Penis

2.1.1.1.2.2 The Scrotum

2.1.1.1.2.3 The Prostate Gland

2.1.1.1.3 On Anybody

2.1.1.2 What's Similar to What (and Why)

2.1.2 Sexual Response

2.1.2.1 The Sexual Response Cycle

2.1.2.2 The Difference Between Orgasm and Ejaculation

2.2 Masturbation

2.2.1 Benefits

2.2.1.1 As a Form of Sexual Exercise

2.2.1.1.1 For Staying Sexually Active

2.2.1.1.2 For Orgasmic Practice

2.2.1.1.2.1 For Women: Learning How to Come

2.2.1.1.2.2 For Men: Learning How NOT to Come

2.2.1.2 As a Tool for Self-Discovery

2.2.1.3 As an Aspect of Self-Sufficiency

2.2.1.4 As a Means of Enjoyment

2.2.2 Advice

2.2.2.1 For Women

2.2.2.1.1 Stuff That Makes Masturbation MUCH Easier

2.2.2.1.1.1 The Basic Options

2.2.2.1.1.1.1 A Vibrator

2.2.2.1.1.1.2 A Shower Massager

2.2.2.1.1.2 Enhancements to Your Vibrator

2.2.2.1.1.2.1 Dildos (and Lube)

2.2.2.1.1.2.2 G-Spot Toys

2.2.2.1.2 Vibrator Technique

2.2.2.1.2.1 Basic Focus on the Clitoris

2.2.2.1.2.2 Things You Can Experiment with After a While

2.2.2.1.2.2.1 Backing Off for Easier Multiple Orgasms

2.2.2.1.2.2.2 Breathing Regularly

2.2.2.1.2.2.3 PC Muscle Contraction

2.2.2.1.3 Later On: Including Masturbation in Partner Sex

2.2.2.2 For Men

2.2.2.3 For Everyone: Erotica

2.3 Sex with a Partner

2.3.1 Basic Stuff to Keep in Mind

2.3.1.1 No Two People Are the Same (Hence, Communication...)

2.3.1.2 Common Gender-Based Differences

2.3.1.2.1 What Men Should Know About Women

2.3.1.2.1.1 Clitoral Stimulation is Usually Needed for Orgasm

2.3.1.2.1.2 Lube Makes Sense for Penetrative Sex

2.3.1.2.1.3 Arousal Often Takes Longer

2.3.1.2.2 What Women Should Know About Men

2.3.1.2.2.1 Arousal Generally Doesn't Take as Long

2.3.1.2.2.2 Firm Contact Can Feel Good

2.3.1.2.2.3 Sex After Ejaculation is Generally Less Fun

2.3.1.2.3 What this Means for Men and Women Together

2.3.1.3 Suggestions for Having a Good Time

2.3.1.3.1 Good Memories are Important

2.3.1.3.1.1 Wait for Someone Considerate

2.3.1.3.1.2 Don't Be Too Intoxicated

2.3.1.3.1.3 Know Where the Condoms and Candles Are

2.3.1.3.1.4 Stick With Your Limits

2.3.1.3.2 Honesty Keeps it Fun

2.3.1.3.2.1 Make a Suggestion When Something Doesn't Feel Good

2.3.1.3.2.2 Make a Suggestion When You Realize What You Want

2.3.1.3.2.3 A Sense of Humor Keeps Everything in Perspective

2.3.1.3.3 Anticipation is Sexy

2.3.1.3.4 Self-Confidence is Even Sexier

2.3.2 What There is to Choose From

2.3.2.1 Touchless Sex

2.3.2.2 Outercourse

2.3.2.2.1 With Your Body

2.3.2.2.2 With Your Hands

2.3.2.2.2.1 Relaxation Massage

2.3.2.2.2.2 Erotic Touch

2.3.2.2.2.2.1 On Women

2.3.2.2.2.2.2 On Men

2.3.2.2.3 With Your Mouth

2.3.2.2.3.1 Kissing

2.3.2.2.3.2 Oral Sex

2.3.2.2.3.2.1 On Women

2.3.2.2.3.2.2 On Men

2.3.2.3 Intercourse

2.3.2.3.1 Vaginal

2.3.2.3.1.1 General Tips

2.3.2.3.1.1.1 Using Lube

2.3.2.3.1.1.2 Taking Your Time

2.3.2.3.1.2 Different Ways People Do It

2.3.2.3.1.2.1 With Their Partner's Fingers

2.3.2.3.1.2.2 With Their Partner's Penis

2.3.2.3.1.2.2.1 Positions

2.3.2.3.1.2.2.1.1 Man-on-Top

2.3.2.3.1.2.2.1.2 Woman-on-Top

2.3.2.3.1.2.2.1.3 Rear Entry

2.3.2.3.1.2.2.1.4 Edge of the Bed

2.3.2.3.1.2.2.1.5 Everything Else

2.3.2.3.1.2.2.2 Enjoying it Longer

2.3.2.3.1.2.2.2.1 For Women

2.3.2.3.1.2.2.2.2 For Men

2.3.2.3.1.2.3 With Their Partner's Strap-On

2.3.2.3.2 Anal

2.3.2.3.2.1 General Tips

2.3.2.3.2.1.1 Going Slowly

2.3.2.3.2.1.2 Using Lube

2.3.2.3.2.1.3 Stopping if Anything Hurts

2.3.2.3.2.1.4 Keeping Clean

2.3.2.3.2.2 Different Ways People Do It

2.3.2.3.2.2.1 With Their Partner's Fingers

2.3.2.3.2.2.2 With Their Partner's Penis

2.3.2.3.2.2.3 With a Sex Toy

2.3.2.3.2.2.3.1 Butt Plugs

2.3.2.3.2.2.3.2 Anal Dildos

2.3.2.3.2.2.3.3 Strap-On

2.3.2.4 Everything Else

2.3.2.4.1 Role Playing

2.3.2.4.1.1 Discovering Your Fantasies

2.3.2.4.1.1.1 On Your Own: Thinking Back on Your Best Experiences

2.3.2.4.1.1.2 With Your Partner: ``Keep Talking or I'll Stop''

2.3.2.4.1.2 Acting Out Fantasies With Your Partner

2.3.2.4.1.2.1 The Four C's of Role Playing

2.3.2.4.1.2.1.1 Clarity

2.3.2.4.1.2.1.2 Creativity

2.3.2.4.1.2.1.3 Clothing

2.3.2.4.1.2.1.4 Confidence

2.3.2.4.2 Expanded Orgasms

2.3.2.4.2.1 Basic Tips for Stronger Orgasms

2.3.2.4.2.1.1 Teasing

2.3.2.4.2.1.2 Kegels

2.3.2.4.2.2 Some Different Ways Multiple Orgasms Can Happen

2.3.2.4.2.2.1 For Men

2.3.2.4.2.2.2 For Women

2.3.2.4.2.3 Spirituality-Influenced Approaches to Sex

2.3.2.4.2.3.1 What We're Talking About Here

2.3.2.4.2.3.2 Is All This For Real?

2.3.2.4.2.3.3 Non-Religious Suggestions Anyone Could Enjoy

2.3.2.4.2.3.3.1 Before Getting Together

2.3.2.4.2.3.3.1.1 Making Time for Your Partner

2.3.2.4.2.3.3.1.2 Creating a Sensuous Atmosphere

2.3.2.4.2.3.3.1.3 Clearing Your Mind of Other Thoughts

2.3.2.4.2.3.3.2 The Physical Side of Sex

2.3.2.4.2.3.3.2.1 Making the Whole Body Feel Cared For and Good

2.3.2.4.2.3.3.2.2 Having Sex that's Fun for Everyone

2.3.2.4.2.3.3.2.3 Breathing Rhythmically and Attentively

2.3.2.4.2.3.3.3 The Emotional Side of Sex

2.3.2.4.2.3.3.3.1 Paying Attention to Your Partner

2.3.2.4.2.3.3.3.2 Focusing on How Much Your Partner Means to You

2.3.2.4.2.3.3.3.3 Staying Aware of Your Body

2.3.2.4.3 BDSM

2.3.2.4.3.1 The Way of Subtraction

2.3.2.4.3.1.1 Blindfolding

2.3.2.4.3.1.2 Bondage

2.3.2.4.3.2 The Way of Addition

2.3.2.4.3.2.1 Soft Sensations

2.3.2.4.3.2.2 Medium Sensations

2.3.2.4.3.2.2.1 Scratching

2.3.2.4.3.2.2.2 Pinching

2.3.2.4.3.2.2.3 Spanking

2.3.2.4.3.2.3 Heavy Sensations

2.3.2.4.3.2.3.1 Paddling

2.3.2.4.3.2.3.2 Flogging

2.3.2.4.3.2.3.3 Caning

2.3.2.4.4 Fisting

2.4 Common Sexual Health Concerns

2.4.1 Safer Sex

2.4.2 Birth Control

2.4.3 Body Image and Lifestyle

2.4.3.1 The Difficult Balance

2.4.3.2 The Benefits of Regular Exercise

2.4.3.3 Feeling Better About Your Body

2.4.3.3.1 Participating in Clothing-Optional Events

2.4.3.3.2 No Longer Putting Yourself Down

2.4.3.3.3 Taking Your Partner's Point of View

2.4.3.3.4 Getting a Therapeutic Massage

2.4.3.4 Feeling Attractive and Sexually Satisfied at Any Size

2.4.3.4.1 Attitude

2.4.3.4.2 Style

2.4.3.4.3 Sex

3 Orientation

3.1 The Three Basic Questions for the Questioning

3.2 Coming Out

4 Gender

4.1 The Three Conceptual Gender Leaps

4.1.1 Not Everyone is Born with ``Textbook'' Male or Female Genitalia

4.1.2 Some Aspects of Gender are Separate from Sexual Biology

4.1.2.1 External Presentation

4.1.2.2 Personal Identity

4.1.3 Some Things Which Appear to be About Gender Identity Are Not

4.2 A Contemporary Concern: The Risk of Physical Violence

4.3 The Bottom Line: Courtesy

5 Community

5.1 The Point of All This

5.2 What's Currently Out There

5.2.1 The Traditional Stuff

5.2.1.1 Swinging

5.2.1.2 BDSM

5.2.1.3 Polyamory

5.2.1.4 Same-gender Sex Events

5.2.1.4.1 Men-only

5.2.1.4.1.1 Bathhouses and Sex Clubs

5.2.1.4.1.2 ``J/O'' Parties

5.2.1.4.2 Women-only

5.2.1.5 Fetish Communities

5.2.1.5.1 The Most Common Ones

5.2.1.5.1.1 Clothing

5.2.1.5.1.2 Shoes and/or Feet

5.2.1.5.2 Everything Else

5.2.2 Emerging Trends and Future Predictions

5.2.2.1 The ``More Things Unite Us than Divide Us'' Trend

5.2.2.1.1 The CSPC Example

5.2.2.1.2 The Dark Odyssey Example

5.2.2.2 The ``Cuddling'' Trend

5.2.2.3 My ``Strange Rebirth of Anonymous Sex'' Prediction

5.3 Supporting Your Chosen Community

5.3.1 Volunteering

5.3.2 Coming Out

5.3.3 Political Activism

5.3.4 Philanthropy

5.4 Creating Something New

5.4.1 Deciding What is Needed in Your Area

5.4.2 Talking To Your Partner About It

5.4.3 Experiencing the Best of What's Out There

5.4.4 Making the For-Profit/Non-Profit Decision

5.4.5 Finding the Next Few Organizers

6 Closing Words

6.1 If You'd Like to Learn More

6.2 Best Wishes!

1 Introduction

1.1 What We'll Be Covering

We'll start with the basics of human sexual anatomy and response, then continue with a discussion of what can make each of the most popular kinds of sex more pleasurable and comfortable. After a brief discussion of several common sexual health issues we'll move on to gender and orientation, and conclude with an overview of some of the various sex-positive communities which exist today.

The writing is going to be frank and direct, and concise enough for most people to feel comfortable reading this guide from beginning to end.

A fun, safe, and passionate sexual life is one of the delights of being alive, and the goal of this guide is to help make that a reality.

1.2 What We'll Leave to the Professionals

The following topics, however, will not be addressed in this guide. Please understand that this is emphatically not because I consider them unimportant, but rather because I want you to have the most current medical information possible: your health is too important to entrust to online advice which may eventually go out of date.

1.2.1 STD Differential Diagnosis

Since some types of sexually transmitted disease may go years before presenting visible symptoms, since some may never present visible symptoms, and since when visible symptoms do appear they're often much harder to distinguish than in the extreme cases captured by typical medical photography, there's almost no point as a member of the general public in looking at unpleasant genital photographs of what STD signs can look like: the bottom line is that if you have any reason to believe you or your partner has been exposed to an STD, then in order to know for sure a test has to be done. Period.

Fortunately, tests are available for a wider range of STDs than ever before, tests which used to require an uncomfortable swab can now often be accomplished with a simple urine sample, and if it turns out that you actually have something which needs treatment then the potential treatment options are better than ever.

1.2.2 Pros and Cons of Specific Birth Control Methods

If you're female and in the process of selecting a birth control method, then chances are you're considering one of the hormone-based methods: they have extremely high effectiveness rates, nothing can really ``go wrong'' with them during sex, they don't require any skill to use, and they're widely available. However, there are specific questions your doctor will need to ask to determine whether they're right for you, and since they're only available with a doctor's prescription anyway, I don't believe any good would be served here by reprinting contraindication and side-effect information for specific products that would only go out of date.

Additionally, there's the fact that new birth control methods become available from time to time (two examples being the 2001 introduction of NuvaRing®, a hormonal vaginal ring which then became an alternative for some women who would have otherwise chosen a hormonal birth control pill, and the 2001 introduction of Mirena®, a hormonal intrauterine device which then became an alternative for some women who would have otherwise chosen a traditional IUD).

So, since I believe you deserve information that is as accurate as it is complete, the pros and cons of specific birth control methods is another discussion topic that will be left between you and your doctor.

1.2.3 Sexual Side Effects of Specific Prescription Medications

Many popular medications have sexual side effects, and new medications with sexual side effects are introduced every year. Ultimately there is no substitute for discussing your concerns with your doctor in a frank manner, and returning to inquire about alternate courses of treatment if the current one is causing sexual dysfunction or distress for you.

It's important to remember that even if you live in a small town your doctor still has a medical degree, and is unlikely to be shocked or embarrassed by any reasonable question you might ask.

1.2.4 ``Edge Play''

Even if you've never personally tried them, you've probably at least heard about kinds of sex that involve one partner consensually tying up the other, or pretending for a few hours that they're the sexual ``servant'' of the other, or giving the other a spanking. Within the organized community of people who enjoy these kinds of activities and get together to share their knowledge about them (aka ``the BDSM community''), the term ``edge play'' is often used for consensual play of a particularly extreme nature (including activities for which there's a risk of serious injury if safety precautions are not followed, and including activities which may not even involve sex but which are purely intended to create an unusually high level of pain and/or terror which the participants find thrilling).

It's true that new forms of advanced BDSM play get invented every year, and then fluctuate in community popularity as the years go by. But to me that's not the point: to me the point is that for any complex physical skill, whether it be Latin dancing, playing the oboe, mountain climbing, or safely suspending another human being from the ceiling using rope, you're better off learning that skill from an experienced and knowledgeable instructor than from a book. Fortunately organized education is one of the cultural cornerstones of the modern BDSM community, to the point where I believe it makes the most sense both educationally and socially to take advantage of the classes offered through established BDSM community organizations and conferences if there are advanced BDSM skills you'd like to learn.

1.3 Why I Wrote This

I feel it's always helpful to know where an author is coming from, particularly when it comes to work that's being made available to you for free. Of course writing can be a satisfying activity in and of itself, but here's why I'm personally drawn to sex as my topic:

A little effort can make a big difference.

Sex is one of the greatest sources of pleasure and intimacy in many peoples' lives, often going on to form some of life's most cherished memories. In parallel with this, the misconceptions which make sex less enjoyable than it could be are often very simple ones. So, in sex education, a little effort can make a big difference. In general, I believe it's wise to seek out situations in life where a little effort can make a big difference.

The nature of sex makes it fulfilling to write about.

A major theme in popular movies, fairy tales, and novels is what is lost in going from childhood to adulthood (or by extension from the mythical past to the present). In the popular animated film My Neighbor Totoro you only see the magical creatures when you're very young. At the end of The Lord of the Rings the Elves leave Middle-earth forever. But the one exception to this meta-narrative is sex: the one wonderful thing you lack as a child but gain access to as an adult. As I see it sex is simply how adults play, which to me makes it the most delightful topic basically ever.

But enough philosophy --- let's get started.

2 Sex

2.1 How the Body Works

If all you cared about sexually was reproduction, then you could probably get by knowing the names and functions of only two body parts: ``penis'' and ``vagina.'' But since this guide also assumes you care about pleasure, we'll be covering the names and functions of several more body parts: for example, ``clitoris'' and ``glans.''

In the spirit of ``there are far more things that unite than divide us,'' I feel it's also helpful to know a little bit about what parts of the male and female genitalia developed from the same tissues in the womb, and may feel similar to each other when stimulated during sex: for example, if you're a male going down on a female, it's erotic to know what part of your penis getting licked by her might feel closest to what she is feeling as you lick her clitoris.

All of this, as well as the body's basic sexual response cycle, will be covered in the sections which follow.

2.1.1 Sexual Anatomy

2.1.1.1 What's What

2.1.1.1.1 On Females

2.1.1.1.1.1 External Anatomy

Vulva:

The term vulva collectively refers to the entire external female genitalia, including the labia, clitoris, urethra, and vaginal entrance. In other words, it refers to everything ``down there'' other than the interior of the vagina itself and the reproductive organs the vagina leads to. One common slang term for the vulva is ``pussy.''

Labia:

The labia minora (or ``inner lips'') are the thin inner tissues which serve the purpose of surrounding and protecting the clitoris, urethra, and vaginal entrance. To some people they can look a bit like a flower. The (often hair-covered) skin just around them is referred to as the labia majora or ``outer lips'', though if somebody just says ``labia'' they're generally referring to the labia minora. Women differ in the degree to which the labia majora cover the labia minora, and in the degree to which the left and right sides of the labia minora naturally match. Both sets of labia are very sensitive, and many people claim to find the scent produced by the sweat glands in the labia majora very arousing. At birth, and until such time as it is torn by either some kind of insertion (for example the insertion of a tampon) or inadvertently through activities such as vigorous gymnastics, bicycling, or horseback riding, the area between the labia minora may be at least partially covered by a thin membrane called the hymen. [Side note: since the hymen can clearly be torn through plenty of ordinary activities other than vaginal intercourse, and since some women are born without an intact hymen, only a very ignorant person or culture would take the hymen's absence as saying anything about a female's ``virginity.'']

Clitoris:

The clitoris (or ``clit'') externally manifests as a small bump at the top of the labia minora where the two sides of the labia minora meet, and is partially if not fully covered by a small structure just above the labia minora called the clitoral hood. As women become sexually aroused the clitoris generally becomes slightly larger and harder (aka ``engorged''), duplicating on a smaller scale what the penis generally does when men become sexually aroused. As the clitoris engorges the clitoral hood may also pull slightly back, making it even easier to give the clitoris more of the same attention that got it engorged in the first place. The only anatomical purpose of the clitoris is to provide pleasure, and that it certainly does: direct stimulation of the clitoris is the easiest way for most woman to reach orgasm, and many (if not most) women cannot reach orgasm without the clitoris being stimulated in some way. It's also important to note that the same tissue which forms the visible clitoris travels a ways inside the body: basically what you see of the clitoris is like the very tip of a wishbone, which splits inside the body and travels along underneath the surface of the body on either side of the labia minora. The physical placement of both the internal and external portions of the clitoris (in relation to the vagina) may impact how much indirect stimulation the clitoris receives during intercourse, and like anything else this will vary from individual to individual: yet another reason why reading anything psychological into whether you or your partner can reach orgasm through vaginal intercourse alone is probably wasted mental effort. When it is necessary to distinguish them, the external portion of the clitoris is called the clitoral glans and the internal portion is called the clitoral body (before it splits into two parts) and the clitoral crura (after it splits).

Urethra:

The urethra is located between the clitoris and the vagina, and serves as the tiny opening through which urine is expelled from the bladder.

2.1.1.1.1.2 Vaginal Anatomy

Vagina:

The vagina is the muscular path which leads inside the body to the female reproductive organs, and which is featured in the style of sex so frequently glorified in poetry and song. The entrance to the vagina is located between the labia minora, below the urethra. It's important to note that the vagina isn't just a ``hole'' which is somehow always open, or which (in similarly incorrect thought) can somehow become permanently ``loose'' as a normal result of having an active sex life: rather, think of it as a cylindrical muscle whose walls normally lie against each other unless there is something between them, and which like any other muscle becomes stronger rather than weaker when exercised. With increased sexual arousal special glands inside the vagina secrete a natural lubrication which makes intercourse easier and more enjoyable for everyone involved, though like any natural process the degree to which this happens will vary according to many factors including time of life. It's also important to note that the shape of the vagina will gradually change as a woman's sexual arousal increases (via the cervix slightly shifting position) in such a way that effectively gives it more length.

G-spot:

``G-spot'' is the popularized term for a specific area of the vagina, located a few inches in and towards the front of the body, which many women find offers a pleasurable feeling when it receives firm pressure during high arousal. Although there is a lot of available discussion and research on which anatomical structures are involved in its effects, the term ``G-spot'' technically refers only to an area of the body rather than to a distinct anatomical structure of its own (in other words, you will not find it in standard medical diagrams).

2.1.1.1.2 On Males

The penis is the part of the male genitalia which becomes erect during sexual arousal. Technically, the term does not include the scrotum, which hangs underneath the penis and contains the male testicles.

Common slang terms for the penis include ``cock'' and ``dick,'' while common slang terms for the testicles include ``balls'' or ``nuts.''

2.1.1.1.2.1 The Penis

Although this knowledge doesn't play a role in sexual technique per se, since this document is going to be published on the internet I'd like to begin by mentioning the three internal parts of the penis which act together to create an erection: the two corpora cavernosa and the one corpus spongiosum. The significant fact is that these are not muscles which make the penis erect by clenching, nor are they bones which make the penis erect by extruding or moving: instead, they're sponge-like tissues which make the penis erect by filling with blood. This means that the natural length of an erect penis is not dictated by the size or strength of any kind of muscle, nor by any other kind of tissue that is known to naturally grow in a healthy adult, and as such you should not be surprised to learn that the various penis enlargement pills and lotions advertised via spam e-mail are generally scams.

The glans is the head of the penis, which in uncircumcised adults is generally at least partially covered by the foreskin whenever the penis is not erect. By contrast, the longer cylindrical part of the penis behind the glans is called the shaft. Since the glans contains a higher density of nerve endings than the shaft, it is particularly sensitive. For many men the underside of the glans is the most sensitive part of the penis, though skin-to-skin contact there is usually more pleasurable if the glans surface is at least slightly moist: fortunately nature provides a helping hand in this regard, since with sexual excitement a few drops of pre-ejaculate (or ``pre-come'') are often secreted via the urethra. Another particularly sensitive area is the coronal ridge, the raised ridge of flesh which separates the shaft from the glans.

The thin strip of flesh underneath the glans (where the foreskin is attached on uncircumcised males) is called the frenulum, and the similar ridge which extends down the underside of the shaft of the penis is called the penile raphe (though this term is in much less common use). Both are extremely sensitive.

In other words, the theme here is that the glans of the penis is generally more sensitive than the shaft, and the bottom side of the penis is generally more sensitive than the top side.

2.1.1.1.2.2 The Scrotum

To recap, the scrotum is the thin pouch of skin and muscle which holds the testicles suspended underneath the base of the penis (the purpose being to lower the temperature of the testicles by keeping them away from the rest of the body, hence increasing the viability of the sperm they produce). The scrotum is a very sensitive part of the body, and can feel very good when handled during sex play: in particular holding the scrotum from underneath (or gently squeezing the testicles) can provide a feeling that may be experienced as sexy and perhaps vaguely comforting, and some men find that gently tugging downwards on the testicles will delay ejaculation. Men differ in how much pressure they like, though many enjoy firm and confident pressure.

2.1.1.1.2.3 The Prostate Gland

The prostate gland is an internal structure, behind the base of the penis and just beneath the bladder, which wraps around the duct that leads to the urethra. It produces a portion of the fluid that semen is made out of, and can often be felt about two inches inside the anus if you press your finger towards the base of the penis. Many men find pressure against the prostate gland (which by its nature also slightly stimulates the base of the penis) to feel pleasurable or at least interesting, particular when they are very aroused or close to orgasm.

2.1.1.1.3 On Anybody

For either men or women, the anus is a very sensitive area that is particularly rich in nerve endings. For almost anyone, even light pressure or circling strokes around the exterior of the anus can feel good --- or at least interesting. For some, penetration of the anus (perhaps with a lubricated finger, or in the shower) can carry an erotic charge, especially when sexually aroused. For men, there's the potential for stimulation of the prostate gland during anal penetration, along with indirect stimulation of the base of the penis. For women, there's the fact that the wall of the anus is very close to the wall of the vagina, plus the fact that internal portions of the clitoris may receive indirect stimulation during anal penetration. As a result, anal stimulation or penetration is a popular and pleasurable part of sex for many people.

The short passageway between the exterior of the anus and the rectum is called the anal canal, and the area between the exterior of the anus and the genitals is called the perineum.

Ultimately almost any patch of skin on the body that has a high density of nerve endings will end up being an ``erogenous zone'' for some people. The lips are rich in nerve endings, so many people enjoy kissing. The fingertips are rich in nerve endings, so many people enjoy having their fingers licked or sucked. The nipples are rich in nerve endings, so many people enjoy having their nipples stroked, sucked, or pinched. And, ultimately, the anus is no different.

2.1.1.2 What's Similar to What (and Why)

The biological term is ``homologous,'' in this context meaning that particular parts of the male genitalia and female genitalia actually grow from the same tissue as the human body develops in the womb. For anyone who has opposite-sex partners, I personally feel this is an ideal way to understand what sex may feel like for your partner in terms that you can personally understand.

The best example is the female clitoris, the external part (or ``glans'') of which is homologous to the head (or ``glans'') of the penis. As such, for both men and women, these are the most sensitive parts of their sexual anatomy. Also, for both men and women, the underside of their glans is often particularly sensitive. Furthermore, for both men and women, direct contact with the glans may be too intense to feel good (or may just flat out not feel good) immediately after reaching an orgasm through stimulation of the glans. By contrast, one difference is that the glans of the clitoris is smaller than the glans of the penis, and hence has an even higher density of nerve endings.

Meanwhile, the longer internal portion of the clitoris (i.e. the clitoral ``body'' and ``crura'') is homologous to the male corpora cavernosa (which as was discussed earlier are internal structures of the penis).

So, if you're male and want a better sense of what your girlfriend experiences during sex, imagine that the head of your penis was smaller but more sensitive, while the shaft of your penis was surrounded by some kind of insulating fabric to where stroking it still felt sexy and still made you feel desired, but might not be enough to let you physically reach orgasm. With this analogy in mind, stroking the head of your penis with a slippery hand might be a little bit like what your girlfriend experiences during oral sex, and stroking the shaft of your penis through this insulating fabric might be a little bit like what your girlfriend experiences (at least physically) during intercourse.

On the other hand, if you're female and want a better sense of what your boyfriend experiences during intercourse, then imagine that your clitoris were much longer, and although the tip was still the most sensitive part the sensations at the tip were a little more diffuse. Also, imagine that any part of this longer, external clitoris was sensitive enough to where you could easily reach orgasm by stroking it. So, with this analogy in mind, stroking the full length of this imagined clitoris with a slippery hand might be a little bit like what your boyfriend experiences (again, at least physically) during intercourse.

In the accompanying table you'll find the homologies between the other parts of the male and female genitals, though if your intent is to understand sexual pleasure then the examples we've just discussed are by far the most illuminating ones. Note that many people consider the male prostate gland to be the equivalent of the female G-spot, even though technically one is a term for a distinct part of the anatomy, while the other is the popular term for a region of the body rather than the distinct parts of the anatomy which may cause its effects. Note also that the Skene's glands are located within something called the ``urethral sponge,'' and that the Skene's glands are sometimes referred to as the ``paraurethral glands'' (both terms being commonly used in writings about the G-spot).

Sexual Homology

Male Anatomy	Female Anatomy
Glans penis	Clitoral glans
Corpora cavernosa	Clitoral body and crura
Corpus spongiosum	Vestibular bulbs
Prostate gland	Skene's glands
Skin on shaft of penis	Labia minora
Scrotum	Labia majora
Testicles	Ovaries
Foreskin	Clitoral hood
Cowper's glands	Bartholin's glands

2.1.2 Sexual Response

2.1.2.1 The Sexual Response Cycle

College textbooks on human sexuality usually devote a lot of space to the ``sexual response cycle'': the physiological changes that take place during the course of a sexual encounter. For example, in their landmark research Masters and Johnson broke the process down into an excitement phase (when the heart rate and blood pressure go up, the clitoris and penis become engorged and possibly more erect, the vagina begins to lubricate itself, and the penis may secrete a few drops of pre-ejaculate), a plateau phase preceding orgasm, an orgasm phase (for both men and women involving the pleasurable rhythmic contractions that we refer to as ``orgasm,'' and in men involving at a minimum an increasing feeling of ``inevitability'' associated with seminal fluid gathering in the upper urethra in preparation for ejaculation), and a resolution phase (in which the body begins to calm down). For men --- particularly if ejaculation accompanied their orgasm --- their resolution phase will generally include a ``refractory period,'' in which no kind of sexual stimulation will cause their sexual response cycle to begin again.

However, although I believe knowing sexual anatomy is helpful for everyone, I'm not convinced that for most people knowing all the technical details about the sexual response cycle is equally helpful: on the one hand everyone is a little different and hence each part of the cycle may be differ in intensity or length, but more to the point you probably already understand your own sexual response cycle, through masturbation if nothing else. Hence, at least for those who have opposite-sex partners, I think it makes sense to focus mainly on the differences between the male and female response cycles.

In my opinion the ``refractory period'' described above is the biggest difference, with the biggest implications: it may not always be appreciated by women how quickly (and how for physiological rather than emotional reasons) enjoyment of more sexual stimulation and even the thought of more sex tends to drop off for men after their ejaculation, and it may not always be appreciated by men that their female partners may still be able to enjoy sex after an orgasm. Taken together this suggests that for many mixed-gender couples it may make the most sense for the female partner to have an orgasm first (probably through stimulation that includes her clitoris), before moving on to intercourse.

This is a theme we'll be revisiting in sections to follow.

2.1.2.2 The Difference Between Orgasm and Ejaculation

Returning to the male side of things for a moment, there's an important distinction which needs to be made: the difference between orgasm and ejaculation. Although many men are used to thinking of these terms interchangeably, the difference is that the former refers to the pleasurable rhythmic contractions which make ``coming'' feel good, while ``ejaculation'' refers to the actual expulsion of seminal fluid. The point is that by learning to experience orgasm (or something very close to orgasm) without ejaculating, it may be possible to avoid most or all of the aforementioned refractory period. Various methods for accomplishing this have been espoused over the years, the simplest of which is to simply pay attention to when you are about to reach the point of ``ejaculatory inevitability,'' and reduce the intensity of whatever you are doing so that you barely reach that point but do not cross it. This way, you may get to enjoy some of the rhythmic contractions which make orgasm pleasurable, but still retain your erection and be able to continue having sex afterward. This is another theme we'll be revisiting in sections to follow.

Since the word ``coming'' can mean either orgasm or ejaculation, we'll use the more specific terms when the distinction matters.

2.2 Masturbation

Most newer sex manuals contain a chapter on masturbation, and a trend seems to be for that chapter to come before any chapters on having sex with a partner. This guide is no exception to that trend, and for good reason: masturbation has real benefits beyond the obvious one (i.e. pleasure), and it represents the one form of sexual release which will be available to you throughout your life regardless of the course your life takes.

2.2.1 Benefits

2.2.1.1 As a Form of Sexual Exercise

2.2.1.1.1 For Staying Sexually Active

Simply put, masturbation is a way to feel sexually active and maintain an erotic dimension to your life regardless of whether you have a regular sex partner or not.

2.2.1.1.2 For Orgasmic Practice

2.2.1.1.2.1 For Women: Learning How to Come

Imagine there's a trail which leads from your house to a friend's house. The more you travel this trail the more easily you'll remember how the trail goes, until you can clearly remember any part of it, immediately know in relation to both of your houses where you are at any point on it, and instinctively know which turns you need to make to get from one end to the other.

Masturbation is the same way. Although there are obviously emotional dimensions to sex with a partner, figuring out what kind of stimulation most easily gets you off, and learning what the path to orgasm feels like, is essentially like any other physical skill: as you practice it, you get better at it.

The flip side of this, of course, is that you'll be in a better position to guide your partner in what they can do during sex to help you feel good: even if doing so feels awkward the first time, the benefits can last the lifetime of the relationship.

Masturbation can also be a good way to experiment with different kinds of stimulation that might eventually carry over into sex with a partner (examples might include experimenting with multiple orgasms and/or G-spot stimulation).

2.2.1.1.2.2 For Men: Learning How NOT to Come

Because of the ``refractory period'' (i.e. the period of time after ejaculation during which you cannot get another erection, and after which it will probably take you even longer to get to the same level of arousal) the orgasmic training benefits of masturbation are a little different for men than for women: you're still learning what the path to orgasm feels like, and in particular you're hopefully learning to recognize the physical sensations immediately prior to the ``point of no return,'' but instead of plowing right through into ejaculation you'll probably want to hang out for a while just before the ``point of no return,'' reducing stimulation as needed so that you don't go over that point into ejaculation.

Then, during intercourse with a partner, you'll be familiar enough with these sensations to be able to (perhaps) thrust less rapidly or deeply as needed to avoid crossing the ``point of no return,'' and hence hang out at that especially pleasurable state for even longer.

Your partner probably won't mind.

Along the same lines, masturbation is also an ideal way to experiment with some of the various ``multiple orgasm'' techniques for men: you may find them worthwhile or you may not, but there is certainly no harm in giving some of them a shot and forming your own opinion.

2.2.1.2 As a Tool for Self-Discovery

During masturbation it's even more obvious what fantasies work for you.

Of course, it's important to keep in mind that the fantasy world is not the same as the real world, just as seeing a documentary about ocean life doesn't mean you just breathed water. However, in some cases you may be able to identify enjoyable fantasies that there might be some safe and consensual way for you and your partner to sample in real life.

Costume supply stores do carry pirate outfits, after all...

2.2.1.3 As an Aspect of Self-Sufficiency

I can't say it any better than Rachel Venning and Claire Cavanah did in their wonderful book Sex Toys 101: ``Learning how to get yourself off is as important for self-sufficiency and emotional intelligence as knowing how to cook a meal or make a friend.''

2.2.1.4 As a Means of Enjoyment

Last but not least: pleasure. Masturbation feels good. In addition to the pleasure of the sex itself, there's the fact that depending on the time of day and how your body responds, an orgasm may leave you feeling energized and relaxed for the rest of the day, or may help you drift off into a wonderful nap (I personally find that in the afternoon a good orgasm can lead to wonderful time-dilated naps with especially vivid dreams).

2.2.2 Advice

2.2.2.1 For Women

2.2.2.1.1 Stuff That Makes Masturbation MUCH Easier

2.2.2.1.1.1 The Basic Options

2.2.2.1.1.1.1 A Vibrator

Getting a vibrator is the single biggest step most women can take towards an improved sex life, whether on their own or with a partner (though note that for now we're speaking of vibrators meant to stimulate your clit, i.e. ones shaped for external use). Of course you can use your fingers instead, but reaching orgasm is usually easier with a vibrator. Please see this document's accompanying sex toy guide at http://www.sexuality.org/sextoys.html for specific product recommendations.

2.2.2.1.1.1.2 A Shower Massager

Although vibrators are nice because you can use them while relaxing in bed, and because you can more easily incorporate them into penetrative sex with a partner, there's still also a lot to be said for shower massagers. To start with, you may already have one in your house. But more to the point, if you have a large family or serious privacy concerns, then the advantages of shower massagers are that there's nothing for anyone to find or overhear, and that the bathroom may be the one place in the house where you have some privacy.

2.2.2.1.1.2 Enhancements to Your Vibrator

2.2.2.1.1.2.1 Dildos (and Lube)

The satisfying feeling of having something just the right size inside you, which your vaginal muscles can bear down on during orgasm, makes dildos an ever-popular sex toy and a great enhancement to the sensations provided to your clit by your vibrator. As with any kind of vaginal penetration, having some kind of water-based lube to use with the dildo can make using it feel even better.

2.2.2.1.1.2.2 G-Spot Toys

Although not all women find G-spot stimulation to be that big of a deal, and not all women find it to be enjoyable, if you're going to enjoy it you'll probably find it more enjoyable the more aroused you are. So, masturbation can be an ideal time to experiment with finding and stimulating your G-spot. Special curved, rigid toys have been created to make this easier for you to do on your own.

2.2.2.1.2 Vibrator Technique

2.2.2.1.2.1 Basic Focus on the Clitoris

Assuming you have some kind of vibrator that's intended for use on your clit, using it is not a complex activity: you turn off the phone if you can, relax into a comfortable position, turn the vibrator on and put it on your clit, maybe move it around in slow circles if that feels good, think about sexy things, and in all likelihood eventually have an orgasm. And even if you don't have an orgasm, it will probably still feel pretty good.

If the vibrations are too strong for your tastes even with the vibrator on its lowest setting, then perhaps use it through panties or even a thin cloth.

2.2.2.1.2.2 Things You Can Experiment with After a While

2.2.2.1.2.2.1 Backing Off for Easier Multiple Orgasms

If you like, you can play around with different sensations after your first orgasm, just to see what happens. Women vary in the degree to which this works or feels good, but if you move the vibrator just off of your clit but keep it running, you might be able to ramp things back up pretty quickly and enjoy a second orgasm.

2.2.2.1.2.2.2 Breathing Regularly

Breathing just a little more deeply and regularly, while perhaps pursing your lips so that you can feel your breath as you inhale and exhale (nobody knows why that makes a difference but it often seems to), may result in longer and more drawn out orgasms. Of course no two people are the same, so if you find this doesn't change anything for you then don't sweat it (so to speak...).

2.2.2.1.2.2.3 PC Muscle Contraction

The pubococcygeal muscle, or ``PC'' muscle, is same one as is involved in Kegel exercises. To contract it, just contract the same muscles you would contract if you were urinating and wanted to stop the flow of urine. If you contract them rhythmically as you lead up to orgasm, then the orgasm itself may be stronger. Once again, though, your mileage may very: as with all of these suggestions, think of them as beginning points for exploration.

2.2.2.1.3 Later On: Including Masturbation in Partner Sex

Just about everybody finds it sexy when their partner has an orgasm during sex with them. For intercourse, using a vibrator might be particularly easy if you're on all fours, though if you have a smaller vibrator (perhaps one of the egg-shaped or lipstick-shaped designs) then it might also work well if you're on your back.

2.2.2.2 For Men

For most men, masturbation is perfectly enjoyable with just one hand combined with mental fantasies, and generally the biggest enhancements are to be found not through the addition of new toys but through the technique discussed earlier of learning to recognize the ``point of no return'' (again, so that you can then back off a little and enjoy the most pleasurable part of the masturbatory experience for a longer period of time). The one exception to this is the comfort value of some kind of lube or lotion, particularly if you get chafing.

I admit to some embarrassment over the fact that this section is so much shorter than the preceding one, and hope nobody takes it the wrong way: it's just that sometimes life is simple.

2.2.2.3 For Everyone: Erotica

The primary purpose of pornography/erotica is to enhance masturbation. Of course, some people prefer to shut their eyes and mentally run through their own fantasies, or else to simply enjoy the experience for what it physically is without fantasizing at all. But, if you prefer to masturbate with the help of something sexy to listen to, watch, or read, then in my opinion it's worth spending some time at the beginning figuring out what you enjoy the most. Possible starting points are given in our erotica guide at http://www.sexuality.org/erotica.html

2.3 Sex with a Partner

Sex educators love to talk about masturbation, and with good reason: it's an excellent way to learn about yourself sexually, and since throughout our lives we will always have ourselves as a sex partner, in masturbation their audience is never divided into the ``haves'' and the ``have nots.''

However, the reality is that many readers probably breezed through the previous chapters to get to this one, and likewise with good reason: in sex with a partner, to the physical pleasures of sex are added the mind's entire emotional and instinctual apparatus related to socializing and mating. It's tied in with erotic love, which has inspired some of humanity's greatest art. And for most people, over major portions of their lives it's something they deeply crave in a way that no amount of masturbation can completely satisfy.

So, although I understand the desire to skip ahead to this chapter, I would still urge everyone to review at least the earlier ``Anatomy'' section, as it contains the basic information and terminology on which this chapter is based. I would also urge any female readers who have never had an orgasm to first give their portions of the preceding ``Masturbation'' chapter a go, and would likewise urge any male readers who don't feel like they have any control over when they ejaculate to do the same.

2.3.1 Basic Stuff to Keep in Mind

2.3.1.1 No Two People Are the Same (Hence, Communication...)

No two people are the same, and any stereotype you can think of --- however common --- might not apply to the person you're with. As such there is just no substitute for paying attention to what your partner seems to like and doesn't seem to like, and there is just no substitute for communicating what you each like and don't like.

In theory I could say that and end this section right there, but in practice it's often helpful to have a bit of knowledge about what is common, so that you at least have a starting point.

However, never forget that whatever your partner says about what they like trumps anything written in this entire guide about what many people tend to like: ultimately ``normal'' means nothing, since you're not having sex with a statistic, you're having sex with a person.

2.3.1.2 Common Gender-Based Differences

I want this guide to be useful to people of all genders and orientations, but here I need to admit: if you're a man who has sex exclusively with other men, or if you're a woman who has sex only with other women, then you may not find this ``Differences'' subsection to be that useful.

Unfortunately the differences between male and female anatomy, in a few cases combined with popular myths about sexuality, have created some misunderstandings that need to be addressed directly.

2.3.1.2.1 What Men Should Know About Women

2.3.1.2.1.1 Clitoral Stimulation is Usually Needed for Orgasm

For their role in perpetuating this misunderstanding I must cite the mainstream porn industry: in many mainstream porn videos the actresses are portrayed as having multiple orgasms, almost immediately after penetration, through intercourse alone.

In real life it doesn't generally work like that way.

I understand completely that porn videos are pure fantasy, but they're also the only chance most folks have to see other people have sex, so it's a pity that what they present isn't always consistent with what enjoyable sex is like for most women.

But, I digress...

2.3.1.2.1.2 Lube Makes Sense for Penetrative Sex

Another thing you don't see in mainstream porn is anybody using lube. The reality is that penetrative sex generally feels better for women when everything is nice and slippery, and although the vagina does produce natural lubrication during sexual arousal, most women find that vaginal penetration of any kind feels better with just a little bit more slathered on whatever beloved toy or body part is going inside them.

Of course, if you're using condoms a little extra water-based lube is basically a requirement, since it helps reduce any chance of the condom breaking.

2.3.1.2.1.3 Arousal Often Takes Longer

When you're actively longing for something, getting it is even more satisfying than it would have been otherwise. And although this is true sexually for both men and women, since on the average it takes longer for women to get aroused than men it's something that's particularly important for men to keep in mind.

In other words, at the beginning of sex (particularly if you two haven't had sex for a while), it's generally good to take your time.

2.3.1.2.2 What Women Should Know About Men

2.3.1.2.2.1 Arousal Generally Doesn't Take as Long

If you're in a sexually active relationship with a man, surprise contact with his genitals (e.g. initiating sex by rubbing the front of his pants or backing up against him) can feel good in a way that it probably would not for you. So, at least on a physical level taking the initiative sexually is actually easier for you to do than it is for him to do, and particularly if you two have been enjoying sex together on a regular basis it may be a delightful change of pace.

2.3.1.2.2.2 Firm Contact Can Feel Good

Men differ in how firm contact can be with their penis and scrotum/testicles and still feel good. Sometimes a light teasing touch can be very erotic, inducing quite a bit of desire for more, and sometimes firm contact (i.e. much more than would probably feel good to you on your clit) can feel fantastic. The two big tips are:

1. A lot of men like firm contact, at least sometimes.
2. Whether it be firm or light/teasing, ``confident'' is always a good characteristic for touch to have (i.e. in contrast to ``tentative'').

2.3.1.2.2.3 Sex After Ejaculation is Generally Less Fun

This was touched on in the earlier section on sexual response, but to recap: after ejaculation men tend to go through a ``refractory period,'' during which the sexual response cycle that begins with arousal and generally continues with erection can't begin again. Men differ in how long this period of time will last, but it does represent a difference between men and women that it's good to stay aware of.

Cuddling, of course, is fine: it's just more sexual contact that can sometimes feel like it's ``too much,'' at least immediately after sex.

2.3.1.2.3 What this Means for Men and Women Together

With slightly different physiology and sexual response, there's a potential for frustration in male-female sex that may not arise elsewhere. So considering all of the above, let's state the ``Big Secret'' of male-female sex: It Usually Makes Sense for the Female Partner to Come First.

2.3.1.3 Suggestions for Having a Good Time

The elements of enjoyable sex exist as much in the mind as the body: after all, if that weren't then case then few pleasure-seekers would pursue anything other than masturbation...

2.3.1.3.1 Good Memories are Important

For many people, reminiscing on past sexual experiences is a popular daydreaming topic. So, good sex doesn't just enhance your life in the moment it's happening: memories of that experience have the potential enhance your life in the future.

With that in mind, the following are a few basic tips for improving the memories you end up with.

2.3.1.3.1.1 Wait for Someone Considerate

Particularly if it's your first time having sex, consider waiting for someone you like who likes you back, and who treats you with respect. If this wasn't the case for you way back when then don't sweat it, but since our first sexual experience is usually one we remember with special vividness, it's a nice bonus if your memories of it and the person you were with are positive ones.

2.3.1.3.1.2 Don't Be Too Intoxicated

Particularly if it's your first time with someone and there are limits you'd prefer to stay within, it's a good idea to avoid being too intoxicated: habitually regretting what you did the next day is a poor way to live just in general.

2.3.1.3.1.3 Know Where the Condoms and Candles Are

Keep your sex stuff (lube and condoms at least, and maybe a towel) where you can easily find it. Also, note that a few candles can make a big difference in how sexy a room looks: just be sure to keep them away from anything flammable, and be sure they can't either tip over or cause problems once they burn down.

2.3.1.3.1.4 Stick With Your Limits

There are plenty of fun things to do together other than intercourse, which for some is a bigger step than they're willing to take at the moment. Additionally, for many people a commitment to stick to safer sex is both necessary and important.

If you decide ahead of time what your limits are and then let someone talk you into lowering them in the heat of the moment, it's likely whatever extra fun either of you had at the time will end up being colored later on by feelings of worry or guilt. So, from both a pleasure-positive perspective as well as (e.g. in the case of safer sex) a health and safety perspective, it's wise to stick with the limits you've decided on.

2.3.1.3.2 Honesty Keeps it Fun

2.3.1.3.2.1 Make a Suggestion When Something Doesn't Feel Good

This takes a little self-discipline, and if it's something you haven't done with your partner before then it would probably be a good idea to mention it beforehand. But the idea is that any time something feels uncomfortable for you, to make a sexy suggestion as to how whatever it is could feel better.

Unfortunately it's easy to get into the habit of gritting your teeth and waiting for something to be over, or hoping it gets better, because you're afraid of disappointing your partner or hurting their feelings. In the long run this really isn't good for you, or fair to your partner.

Asking your partner to do something differently, if what they're doing doesn't feel good at the time, can be awkward the first time. It's less awkward the second time. It's much less awkward if you can find a sexy way to make the suggestion. And before long, discomfort during sex may be only a memory.

I'm not sure who first came up with this, but I've heard many local sex educators repeat it as a guiding principle: ``endure nothing.''

2.3.1.3.2.2 Make a Suggestion When You Realize What You Want

Sexual communication isn't just about speaking up when something is uncomfortable: it's about being able to talk to your partner about what you like. Making your partner guess what you'd enjoy can be frustrating to him or her, but if asked in the right way the request can be sexy for both of you: a win-win situation.

Once again: it may be awkward the first time, but most people find it gets easier very quickly.

2.3.1.3.2.3 A Sense of Humor Keeps Everything in Perspective

I'm not talking about making fun of your partner or anything concerning them, but rather of keeping a sense of humor about sex in general. In a situation that feels a little bit awkward or tense, acknowledging the situation in a funny way can help both of you relax and go back to enjoying the sex.

2.3.1.3.3 Anticipation is Sexy

Looking forward to something increases the enjoyment of it when it actually happens, and in the case of sex keeps you thinking about sex until it happens.

A sexy phone call to your partner doing the day, a sexy note, going to a dance club and teasing them on the dance floor, or anything else that reminds your partner of what they'll get to enjoy later on that night, can all be good things.

2.3.1.3.4 Self-Confidence is Even Sexier

Self-confidence is one of the sexiest characteristics you can bring to sex: if you know your partner wants to be with you, and that he or she considers sex with you to be a treat, then you might as well act like it.

To me, this means a few extra things:

1. Hot talk is almost always appreciated.
2. Don't put yourself down: no flaw you could perceive in yourself or your body is likely to be as unattractive to your partner as you putting yourself down for it.

2.3.2 What There is to Choose From

There's no shortage of sexual acts for you and your partner to choose from: the following will only cover the most popular ones, starting with ``touchless sex'' (stuff that's sexual but which doesn't involve actual contact), continuing with ``outercourse'' (sex that doesn't involve penetration) and ``intercourse'' (sex that does involve penetration), and concluding with ``everything else'' (role playing, BDSM, and more).

2.3.2.1 Touchless Sex

Although I can imagine ``touchless'' forms of sex being good for partners in long-distance relationships, or for people who have extreme concerns about STDs that cannot be addressed in any other way, or for people who are forgoing sexual contact for a period of time for personal or religious reasons, I can't help but mention one other possible use for it: extreme teasing. Basically, if you're accustomed to having intercourse with your partner on a regular basis, then after a few weeks of being continually teased, and coming so close to being touched (but not quite), you'd probably be pretty much ready to explode.

Anyway, here are just a few possibilities:

• You call each other on the phone, and masturbate while talking about what you'd like to do to each other.
• You write each other letters telling each other in graphic detail what you'd like to do to each other, maybe setting a specific date in the future to live that out.
• If you're female, using a vibrator (possibly through your clothes if you don't even want your partner to see you naked yet) while your partner lies very close but doesn't get to touch you.
• Getting very close to your partner, as if you were going to kiss their neck or go down on them, and murmur nasty things to them without actually touching them (this can be pretty cruel, particularly if the recipient loves oral sex but has gone without it for a while).

2.3.2.2 Outercourse

Although there's some disagreement about whether the word ``outercourse'' should include oral sex or not, as used here outercourse refers to all common forms of sex which do not involve penetration of the vagina or anus.

Although (particularly with oral sex) the risk of STD transmission doesn't completely disappear, all other things being equal most kinds of outercourse tend to be lower-risk activities. They don't involve loss of ``virginity'' (as traditionally defined in the heterosexual world), and they ordinarily carry no risk of pregnancy.

Even for partners who have long-since moved into enjoying penetrative sex, these can be wonderful forms of foreplay.

2.3.2.2.1 With Your Body

Also known as ``frottage,'' this amounts to rubbing your body against your partner's genitals (possibly while wearing clothes, possibly not).

Sexy dancing at some of the less inhibited nightclubs can amount to this, as can (for women with male partners) finding a moment of privacy to back up into your partner and rub your butt against them. For women with female partners, it can amount to rubbing yourself against your partner's thigh. Another popular form of frottage is taking a shower together: between the water and all the slipperiness it's a perfect opportunity to rub your body against your partner's in sexy ways.

2.3.2.2.2 With Your Hands

The fingertips are one of the most sensitive parts of the human body, and the hand one of the most versatile. I like to think that hands are to sex what eyes are to everyday life: they're how you ``see'' your partner.

2.3.2.2.2.1 Relaxation Massage

Although this isn't necessarily sexual, it's definitely sensual: being able to give someone a relaxation massage is a wonderful skill, and in the case of a lover can be wonderful prelude to sex (or possibly a wonderful thing to do after sex, if you're feeling especially indulgent...). There's no shortage of books and classes on how to give someone a relaxing full-body massage, but here are a few basic tips:

1. There's just no substitute for having a massage table: it makes things much easier for the person giving the massage, as well as more relaxing for the person receiving it. They aren't that expensive.
2. Although you can use vegetable-based or nut-based oils from the grocery store as a massage oil, you might want to look into massage therapy lotions: they feel very similar, but are less likely to leave oil stains on sheets. Either way, using a small squeeze bottle that won't spill is wise.
3. Don't let your partner get cold: having a sheet on top of the massage table, while they're lying underneath a second sheet and perhaps a thin blanket, is a good idea (they can stay mostly covered up except for where you're working). Alternatively, you can crank the heat in the room way up, or more luxuriously yet put the massage table in front of a fireplace with the room lights dimmed.
4. Confident touch is good touch.
5. For long gliding strokes down the back, lean into them a bit with your body weight rather than depending up upper arm strength: the result is smoother, and feels more reassuring to the person receiving the massage.
6. Particularly if your partner has long hair, or spends a lot of time on their feet, giving them a scalp massage or massaging their feet may provide an experience so pleasurable that it's almost erotic --- no massage table required.

In general, the feeling of relaxation you get after a good full-body massage from your partner isn't that different from the feeling of relaxation you get after sex with your partner: in each case the body's basic need for touch is being satisfied, which authors such as Ashley Montagu have argued is a basic human need.

2.3.2.2.2.2 Erotic Touch

Think of the organization of this entire chapter as follows: we're running through the common sexual acts from the outside of the body inwards (or as some folks will probably think of it, from ``light'' to ``heavy''). So, we'll cover penetration a little later, and this section on erotic touch is just about the outside of the body: helping your partner feel good by using your hands on his penis, or on and around her clit.

2.3.2.2.2.2.1 On Women

They say the secret of show business is ``always leave them wanting more.'' With sex, perhaps, the secret is a bit different: ``don't rush.'' Particularly for women, genital contact before they're at least slightly turned on generally isn't fun, and can be kind of annoying.

But once you two are turned on, there are two directions this kind of sex can go:

1. With the intent of it leading to orgasm.
2. Without the goal of it leading to orgasm, but rather as a fun and arousing form of touch in and of itself (and possibly as a prelude to other kinds of sex).

The distinction is that in the first case the best way to proceed very much depends on what your partner likes: frankly, the best approach is probably to ask her to show you how she likes her clit touched. After all, the feeling of almost getting the right kind of stimulation to get off can be frustrating.

Here are a few things to keep in mind:

1. Women differ in what kinds of clitoral stimulation they like, in whether they prefer fingertips or a vibrator, and in how easy it is for someone else to get them off this way: as always, people differ sexually just as they differ in what kinds of foods they prefer.
2. If your partner prefers a vibrator to fingers, then lucky you: most bedrooms have electrical outlets, and the vibrator can do its magic endlessly without getting tired. Additionally, since strong vibrators can still feel good through clothing, this provides a way to have a satisfying sexual experience for folks who aren't ready to get totally naked together yet.
3. If your partner prefers fingertips to a vibrator, then it would probably make sense to have a little bottle of water-based lube on hand: a small amount on the fingertips can make them feel quite a bit better as they slide over the clit. Note that this once again brings up a basic principle of good sex: slippery is sexy.
4. If your partner prefers fingertips to a vibrator, then keep in mind that different parts of the clit feel different: if direct contact on the tip of the clit feels too intense to your partner, then sliding along the sides of the clit might feel just right.
5. Particularly as your partner approaches orgasm, it's usually best not to change whatever you're doing.
6. The fun thing about this kind of sex, in comparison to oral sex, is that your mouth is free to say sexy things to your partner, or kiss her.
7. If your partner is very specific in the kind of stimulation she needs to get off, and if even after some practice together she has trouble getting off with your fingers rather than hers, then there's nothing wrong with cuddling, smooching, or spooning while she gets herself off: that can be sexy too, and it's a reminder of the fact that there are countless fun ways to have sex.

2.3.2.2.2.2.2 On Men

Of course learning more about what feels good to the man you're with will make everything better, but in general there are really only two ways you can go wrong when taking your lover's penis or testicles in hand:

1. Being incredibly timid and hesitant in what you're doing.
2. Using too much friction (e.g. your hand firmly sliding over the skin of the shaft of his penis for far too long when both surfaces of skin are completely dry): slippery good, chafing bad. [Note: for an interesting change of pace, try using silk gloves rather than lube...]

Beyond those two basic suggestions, it's more a question of taking something that already feels good and making it feel even better. Here are some tips:

1. Always remember the big benefit of this kind of sex: your mouth is free for saying nice things. General sexy talk, perhaps a lurid description of what he gets to do with you after this, or perhaps nothing more than general patter about how good his hard dick feels in your hand, is always a good thing to try. It doesn't have to be anything complex, and in fact it barely even needs to make sense: just hearing sexy words are often enough to add to the experience. If you have your face close to his penis when doing this it can add an extra charge, by adding implicit oral sex fantasies (if not the reality) to the mix.
2. The simplest position for your hand is simply to have your fingers and thumb make a ``tunnel'' shape that can travel up and down the shaft of the penis.
3. If you two are using this as the ``main course'' of sex rather than as a prelude to something else, then it would definitely be best to get hold of some kind of lubricant intended for sex, such as the omnipresent water-based lubes; this way you can do long, firm strokes as much as you like without anything feeling like it's chafing. If that's not possible, then use use shorter strokes such that the skin covering the penis slides with your hand rather than against it, and go a little faster (this can feel best closer to the head rather than the base of the penis).
4. Remember that you have two hands. For variety, you can try any of the following: using your other hand to cup and support his balls, using your other hand to firmly squeeze the base of the shaft of his penis while your other hand concentrates on the rest of the shaft of his penis, or using your other hand to stimulate the head of his penis (perhaps with your palm once the head of the penis is nice and slippery with a few drops of pre-ejaculate).
5. Good, long, repeated, confident strokes that start at the head of the penis and travel its entire length can feel wonderful, particularly after you've been doing something else for a while.
6. If you're female, then you may want to take the opportunity to squeeze your partner's penis between your breasts as part of this kind of sex: many men find that image very sexy.
7. Here's a decadent tip: if you and your partner regularly use this kind of sex as the ``main course'' of sex (e.g. doing it until he ejaculates) then it can be a nice touch to have a warm, wet washcloth on hand for cleanup afterward. That can feel great.
8. If your partner is willing to either show you how he masturbates, or describe it to you, then you may have a good start in learning what feels best to him.

2.3.2.2.3 With Your Mouth

Like the fingertips and hands, the lips are an incredibly sensitive part of the human body. Additionally, with the mouth there's the added charge of this being the same part of the body we associate with eating: another pleasurable, sensuous activity. Plus, oral sex combines touch with taste, for an additional sensory dimension.

For these reasons my guess is that kissing and oral sex will always be popular erotic activities.

2.3.2.2.3.1 Kissing

This is true of just about any aspect of sex, but is particularly true for kissing: it's best when you're enjoying it in and of itself right in the moment --- at each indivisible instant --- rather than thinking ahead about the next activity or even about the rest of the kiss.

Personally, I like to think of a good kiss as a microcosm of sex itself: it starts light, as both people lose themselves in the experience of each other it gets heavier, and it has a lingering, glowing ending.

2.3.2.2.3.2 Oral Sex

Oral sex is a very, very popular pastime. Not everyone loves it, but most people do. And, just on a physical level, oral sex has a lot going for it:

1. The giver gets to enjoy the sensuous feeling of their lover on some of the most sensitive parts of their body (i.e. their lips and tongue), along with their partner's smell and taste.
2. The receiver gets to enjoy nice, wet sexual contact. And as has been mentioned a few times so far: slippery is sexy.

However, I don't believe either of the above represents the biggest reason oral sex is so popular: rather, I believe it's because --- psychologically --- putting your mouth on your partner's genitals, or taking your partner's genitals into your mouth, is just about the most carnal act imaginable. It's primal, it's impulsive, and it's sexy.

But at least to me, that kind of psychological component means this sexual act makes almost no sense whatsoever unless the person giving it genuinely enjoys and looks forward to doing it for their partner.

So, by all means: if you fundamentally don't enjoy giving oral sex, then don't do it. Instead, pick some other sexual activity that you might enjoy doing with your partner more --- after all, it isn't as if there aren't dozens of different kinds of sex to choose from.

However, if you are going to do it, then look towards your own enjoyment: if nothing else pick a position that's comfortable for you, think about what you like about your partner, and think about how good this must feel to your partner.

So, that's the first secret of giving good oral sex: if you choose to do it, then enjoy yourself.

The second secret of giving good oral sex is even simpler: keep your hands busy.

2.3.2.2.3.2.1 On Women

Here's what matters:

1. That your partner knows you're enjoying what you're doing.
2. That you figure out where her clitoris is, asking your partner for guidance the first time if necessary. That's where most of your attention will be focused.
3. That you keep a fun attitude: if your partner offers you a suggestion for something that would feel better (i.e. ``Honey, just a little more to the left...''), understand that it's probably something that will make a big difference to her, and it's nothing you could have known about otherwise.
4. If your partner starts getting close to coming, then don't change what you're doing: keep doing exactly the same thing.
5. If your partner is OK with this, then after a while it might feel good to tease the opening to her vagina with your fingers while going down on her, or use two fingers for vaginal penetration (more on that later).

2.3.2.2.3.2.2 On Men

Here's what matters:

1. That your partner knows you're enjoying what you're doing.
2. Despite the fact that ``blow job'' is one slang term for going down on a man, it really has nothing to do with ``blowing.'' Whether you're taking your lover's penis in your mouth, or running your mouth along the shaft of your partner's penis, it's all about the pressure of your lips and your tongue against your partner. Together with whatever you're doing with your hands for the lower shaft of his penis or for his testicles, that's pretty much it.
3. Avoid scraping your teeth against your partner's skin: that doesn't feel good to most men, and can make your partner nervous...
4. Particularly after a few minutes of oral sex, spending a little time focusing on the head of your partner's penis, or the bottom side of his shaft, can feel good: those are particularly sensitive areas.
5. It feels good if you can give all of your partner's genitals at least a little attention: if nothing else running your hands around and under his balls can make everything feel nice and ``included.''
6. Using your hands is one of the big secrets of going down on men. For example, you can use one hand towards the base of his penis, moving in unison with your mouth, to make it feel like you're taking all of him in your mouth. Alternatively, you can mainly use your mouth and tongue around the head of his penis, and use your hand on the rest of his shaft with a smooth stroking motion. Finally, you can use one hand wrapped around the base of his shaft, and let him thrust: this way there's a limit to how far into your mouth your partner can go, which may increase your comfort level if you're concerned about gagging, or if your partner loves receiving oral sex and sometimes gets carried away. In any case, those are just examples: explore and figure out what feels good for you and your partner.

If you're not using condoms as barriers, and if you're using oral sex as the ``main course'' of sex and don't plan to move onto something else later, then there's the age-old question of whether to ``let your partner come in your mouth'' or not.

To start with, don't do anything you don't want to do, or that you find distasteful: that's really a bad path to travel just in general when it comes to having a good time with sex, or when it comes to building up trust with your partner. Having said that, if having your partner come in your mouth doesn't appeal to you, here's what you can do instead:

1. Make sure you give your partner some kind of stimulation all the way through his orgasm --- stopping early tends to produce an orgasm that's only a fraction of what it would have otherwise been. Along the same lines, slow down to a stop rather than stopping abruptly.
2. Since (obviously) in this case you're going to want to want to take your mouth off of your partner's penis before he comes, it's nice to find a way to keep ramping things up even while doing this. One possibility is to use your hand the same way you were using mouth (ideally covering some of the same area your mouth just was), but to start saying nasty things to your partner about how you'd love to see him come. Hot talk goes a long way towards making up for whatever your mouth used to be doing, just in general.

2.3.2.3 Intercourse

Here we use the term ``intercourse'' (distinct from ``outercourse'') to mean any kind of sex involving penetration of the vagina or anus.

One thing should be addressed up front: the fact that we're going to be talking about some very intimate activities here, activities which for many people carry a lot of emotional impact. As such it may seem strange to talk about them in such a clinical way, but the thing to remember is that --- ultimately --- sex is about people. So, when reading about an unfamiliar activity, don't just follow along in the abstract: instead, perhaps imagine yourself experiencing that activity with an attractive partner whom you like and trust --- in other words at least trying to imagine a circumstance in which you might find that activity enjoyable.

2.3.2.3.1 Vaginal

2.3.2.3.1.1 General Tips

2.3.2.3.1.1.1 Using Lube

As was discussed earlier, the vagina produces its own lubrication when a woman is sexually aroused. However, the degree to which this happens varies with any number of factors, including ones that are outside anyone's control (e.g. age). So, going back to the ``slippery is sexy'' principle, the first big tip is to have a little bottle of water-based lube (without Nonoxynol-9) on hand for sex. Simply apply a little to whatever is going to be inserted, and reapply whenever things start to feel uncomfortably unslippery.

2.3.2.3.1.1.2 Taking Your Time

This act in particular tends to be more fun for women the more aroused they are, so take your time getting there: any of the activities described earlier in this chapter might be good appetizers.

2.3.2.3.1.2 Different Ways People Do It

2.3.2.3.1.2.1 With Their Partner's Fingers

For women who prefer sex with other women, having their lover's fingers deep inside them while simultaneously enjoying full body contact and deep kissing may be at the absolute top of the sexual intimacy thermometer.

For women who prefer sex with men it doesn't have to mean anything less, and there's a lot to be said for it just in general: you're absolutely free of concerns about contraception failure, you're essentially free of concerns about receiving STDs (assuming your partner's hands have healthy, intact, and clean skin), you can experiment with direct G-spot stimulation in a way that penis-in-vagina intercourse doesn't easily allow, and if you're either multi-orgasmic or else just have enormous stamina, then (partner willing) you can go ahead and enjoy sex for hours on end. And of course, there's nothing stopping you from having your partner turn around so you can go down on him while he's finger-fucking you, or from treating him to his favorite kind of sex afterward.

A few tips:

• To reiterate, fingers are the best possible way to experiment with G-spot stimulation.
• Remember the water-based lube.
• Maybe start with one finger, and before that perhaps begin by teasing the outside of the vagina. But ultimately, after sex has gone on for a while, most women find penetration with the first two fingers of one hand to be just the right amount.
• For a change of pace, while your first two fingers press upward into the vagina, you can use your thumb to strum or trace circles over your partner's clit. That can feel nice.
• Make sure your fingernails are clipped.

2.3.2.3.1.2.2 With Their Partner's Penis

In one sense, it seems strange to relegate this form of sex --- the subject of so much poetry and song in the heterosexual world, and the overwhelming interest of many of the people who seek out information about sex --- to just one subsection in one enormous outline. But keep in mind the bigger picture: that even for heterosexual couples, this is still just one possible form of sexual intimacy among many other possibilities, and that the intent of this entire chapter is to present the full menu of delightful things to choose from.

2.3.2.3.1.2.2.1 Positions

New books on sexual positions get written every year: from a marketing perspective it's a fantastic excuse to publish books containing dozens full-color pictures of attractive people having sex, and probably amounts to a sure bet at the cash register.

However, from a practical perspective:

1. Most of the sexual positions are just slight variations on three or four basic ones.
2. None of the more bizarre and/or athletic ones tend to add anything in terms of pleasure over what the basic ones do.

This isn't to say that working through one of the ``positions'' books can't be fun (a subject we'll revisit a bit little later), but chances are the positions you'll find the most enjoyable and comfortable in the long run will be one of those described below.

In general, it's worth repeating that as enjoyable as the sex may still be, most women cannot reach orgasm without some kind of stimulation directly to the clitoris. Of course, one perfectly viable way to approach sex is for the woman to have an orgasm first, then the rest of intercourse amounts to the guy having his turn. But, the thought of ``simultaneous orgasm'' (even though in my opinion it's perfectly fine to take turns enjoying them) is important to a lot of people, and admittedly it can be fun when it works. So, with that in mind, we'll be sure to mention it if there's a variation on one of the following positions which allows the clitoris to get some direct attention during intercourse.

2.3.2.3.1.2.2.1.1 Man-on-Top

In other words, the classic ``Missionary Position,'' and several variations on it.

This can be a lot of fun, particularly for couples who like to enjoy deep kissing or nasty talk along with their sex. You get full body contact, you get easy and close eye contact, and the person on the bottom can enjoy a nice ``enveloped'' feeling.

Variations include:

1. The woman wrapping her legs behind her partner's back a little further up, for a different angle and a slightly different sensation (or alternatively putting a pillow or two under her bottom, which can achieve largely the same thing).
2. The man supporting more of his weight on his hands (or better yet forearms), particularly if it's hot or his partner is starting to feel squished.
3. The woman can reach her hands over her head and push back against the headboard of the bed, or the wall, for a little extra force in vigorous fucking (not to mention less sliding towards the head of the bed).
4. For especially passionate and vigorous thrusting, the man can press his feet against the foot of the bed so that less energy is wasted sliding around the bed when thrusting (note that it's good to keep these kinds of things in mind when buying a bed --- as much as I love the minimalist style in furniture, beds lacking something raised and solid at their foot are less attractive for this reason). Alternatively, holding your partner's shoulders from underneath, or grabbing something on the headboard, can serve the same purpose.
5. If the man can raise himself up a bit, perhaps supporting his weight on his knees, then although this might not allow thrusting that's quite as deep, it does free the women to rub her clit with her fingers, or apply a vibrator to the same. Then, after an orgasm, everyone is still in a perfect position for more sex.

2.3.2.3.1.2.2.1.2 Woman-on-Top

This position provides the woman with a great deal of control, and for women who find themselves able to reach orgasm through intercourse alone this position may be the easiest one for that to happen in. For women who have a healthy amount of sexual self-confidence, and are so inclined, it's also a great position to tease and talk dirty to their partner in.

If you and your partner are going to be having sex for a long period of time, it also makes sense to switch between this position and one of the others so that everyone gets a turn lying down.

Of course, the partner on the bottom doesn't have to be completely inactive: rhythmic thrusts, as long as they're in rhythm with what his partner is doing, can be a positive thing.

Obviously this position provides good opportunity for clitoral stimulation, as the woman can simply lean back a little bit, supporting herself with one arm and working her clit with her other hand. And who doesn't enjoy a nice, sexy show from time to time?

2.3.2.3.1.2.2.1.3 Rear Entry

This position (also known as ``doggie style'') is popular for a number of reasons:

1. It has a raw, animal edge to it that many people find very sexy.
2. The woman can easily change the angle of penetration for different sensations.
3. This is by far the easiest position in which the clitoris can also be stimulated: the woman can finger her clit, or apply a vibrator to her clit, all without needing a change in position or disturbing anything her partner is doing.
4. Men who love the look of their partner's bottom get to see their partner's bottom.
5. If it's summer and you don't have air conditioning, this position offers less skin-to-skin contact than other positions, so there's less of a chance anyone will start to feel uncomfortably hot or sweaty.
6. Nobody is lying on anybody, so there's less chance anyone will either feel squished or worry too much about whether they're making their partner feel squished.

Obviously one disadvantage of this position is that both people are on their knees, which is why for lengthy sex it may make sense to alternate this position with one of the others.

The other disadvantage is that you don't get to enjoy eye contact with your partner, though I suppose you could arrange a mirror near the head of the bed if you want to take care of that in a nice, sexy way.

Unfortunately (and I hate to have to bring this up) there's one possible disadvantage to this position when having sex with someone new: if you expect your partner to be using a condom, then this position allows him to more easily take the condom off without you noticing. If you trust your new partner and have reason to trust him, then obviously this is nothing to be concerned about, but for casual sex with someone you don't know that well, or while intoxicated in a ``party'' setting, it might not be the wisest position to pick unless you're keeping a very close eye on things.

2.3.2.3.1.2.2.1.4 Edge of the Bed

The man stands up, and the woman lies on her back either on the bed (if it's the right height), or on a massage table, or on one of those special slings especially designed for this kind of sex. To change the angle of penetration, she can either put her feet up on her partner's shoulders, or else (if the edge of the bed or table is close enough) press them against the wall.

Obviously it's incredibly easy for the woman to reach her clitoris in this position. This position also removes any pressure from her stomach or knees, and as such might be ideal for women who either suffer from back problems or are in the early stages of pregnancy.

2.3.2.3.1.2.2.1.5 Everything Else

As we mentioned earlier, there are far fewer sex positions in everyday use than some books might lead you to believe: honestly, even if they've tried many others, most people eventually gravitate towards one or more of the positions described above, simply because they're easy, comfortable, and work well.

Having said that, there is still value in picking up one of those illustrated sex positions books and spending a silly evening trying to go through all of them in order with your partner. Since in doing this the focus has shifted from trying to please each other to just trying to accomplish something together, some of the pressure that might otherwise make one or both of you nervous about sexual communication will hopefully be released in a fun way.

2.3.2.3.1.2.2.2 Enjoying it Longer

Within reason, sex is often sexier the longer it goes. In the case of sex between men and women, the reason may often be that women often take longer to get aroused (perhaps especially if she and her partner aren't having sex regularly), and hence the longer sex goes on the more time she spends in the zone where it's the most fun.

With that in mind, what follows are a few tips on how to enjoy sex for lengthier periods of time.

2.3.2.3.1.2.2.2.1 For Women

Here are the big tips:

1. For any kind of penetrative sex, make sure you have some water-based lube, and reapply a little if things start to feel unslippery.
2. Speak up if anything is making you uncomfortable: for example, if your knees are getting sore from the ``doggie style'' position, then suggest a switch to your partner being on top.
3. It's helpful to keep a water bottle nearby: a nice cool drink at the right time can be very refreshing, and it's silly to have to go all the way to the kitchen to get it.
4. If you're using safer sex supplies, then make sure nothing you're using contains Nonoxynol-9 (this stuff is now considered by the CDC to be a bad safer sex idea just in general, but for sex over extended periods of time it's probably fair to assume it's an even worse idea).
5. If you can queue up several albums in your music player beforehand, and set the entire group on repeat, then do so: going from music to silence can break the mood a little, but hearing the same album over and over can also be a drag.
6. Start earlier in the evening.

2.3.2.3.1.2.2.2.2 For Men

Since after an ejaculatory orgasm men generally go through a ``refractory period,'' which has to be waited out before their sexual response cycle can begin again, what may be most helpful for extended sessions of sex (or at least, any kind of sex that involves their penis) is a high level of body awareness so that their ejaculatory orgasm can be truly saved for the end of the evening.

This was discussed earlier in the chapter on masturbation, but it's worth repeating: using masturbation to learn exactly what your body feels like just before it crosses the ``point of no return,'' and then during sex with your partner either pausing or thrusting more slowly if you're about to cross over this point, are what may make the biggest difference.

In the context of a relationship where you can easily communicate during sex, this opens up potentially any form of sex to be enjoyable for as long as you like.

2.3.2.3.1.2.3 With Their Partner's Strap-On

For women who have sex with other women and would like to try using a strap-on dildo, the critical first step is selecting a quality harness and dildo combination: patronize a shop which caters to women and carries a variety of high-quality harnesses with matching silicone dildos, and which can provide advice to you about proper fit for your body type.

After donning their strap-on, but before continuing sex with their partner, some women find it helpful to spend a few seconds getting used to the toy: perhaps feeling the length of the attached dildo, lightly pressing it back against the pubic bone, and in general letting the mind start becoming aware of this new object that it's going to be expected to use as if it were a body part. This may have a positive impact on how natural using the strap-on will feel.

Other than that, it's all about practicing: even if you select quality gear that's adjusted properly, it may be a little while before using it feels completely natural to you.

2.3.2.3.2 Anal

Although it isn't everyone's cup of tea, there are several good reasons why anal penetration (or even stimulation of the anal opening without actual penetration) is such a popular sexual activity:

1. The anus is very rich in nerve endings, resulting in intense and interesting sensations whenever it is intentionally stimulated.
2. Some men find that anal penetration can stimulate their prostate gland, which (especially when they are already aroused) can put an interesting new spin on the sexual sensations they receive from stimulation of their penis.
3. Some may find an erotic charge in anal sex because they think of it as being somehow ``naughty.'' Others may find an erotic charge in anal sex because the sensation of taking something inside their body may feel so unusual and/or intimate.
4. Wearing a specially-designed toy such as a ``butt plug'' during sex results in different sensations when you move your pelvis. Alternatively, if you practice PC muscle contraction during sex for orgasm enhancement, then you've probably also noticed when you clench your PC muscle the muscles around your anus tighten as well: having something for them to clench around just makes you even more aware of this clenching, in a way that you might find erotic and interesting.

As a side note, I'm told that some heterosexual men are hung up about whether anal penetration will somehow ``make them gay.'' Obviously, having something in your butt doesn't make you gay: being sexually attracted to other men is what makes you gay, and so far nobody has found a way to make that happen for straight men any more than they've found a way to make gay men straight. Put in another way: if having had the experience of, during oral sex, your female partner putting her finger in your anus and you liking the sensation could somehow make you gay, then there would be far, far more gay men in the world than there currently are.

2.3.2.3.2.1 General Tips

2.3.2.3.2.1.1 Going Slowly

Especially with a partner new to any kind of anal play (or who may have had bad experiences with it in the past but wants to give it another try with you) it's important to go slowly, and let the person being penetrated decide when they want more.

Also, keep in mind that anal play doesn't have to mean anal penetration: the outside rim of the anus is very sensitive in and of itself, and running a lubed finger around it can be plenty arousing for some people.

So: start slowly, go slowly, and listen to what your partner is saying.

2.3.2.3.2.1.2 Using Lube

Unlike the vagina, the anal passageway doesn't produce its own lubrication. So, when inserting anything into the anus, lube is in order. The usual water-based lubes (once again, without Nonoxynol-9) are perfectly fine for most kind of anal play.

One caution, however: under no circumstances can I recommend that you purchase any of the anal lubes which are marketed as containing ``numbing agents.'' If anal sex is uncomfortable for you, then examples of productive responses might include asking your partner to go slower, using more lube, using a smaller dildo, or maybe even just skipping the anal play altogether for the time being. By contrast, an example of an unproductive response would be deadening one of the body's natural warning signals.

2.3.2.3.2.1.3 Stopping if Anything Hurts

Anal penetration shouldn't hurt: the tissues involved are delicate, and sharp pain in particular shouldn't be ignored.

2.3.2.3.2.1.4 Keeping Clean

Although Hepatitis A would be a concern if one partner has it and the other isn't vaccinated against it, for many people general cleanliness is their biggest concern about anal play.

Even if so, it isn't necessary to go through anything as drastic as an enema before ordinary kinds of anal play if you want to feel clean. Simpler measures for fastidious folks include:

1. Saving anal play for when you and your partner are in the shower together (note that this isn't a substitute for safer sex barriers if they're needed --- rather it simply may be perceived by some as a cleaner and more comfortable setting for anal play just in general).
2. Donning latex or Nitrile gloves (available at most drugstores) before putting your fingers in your partner, and peeling off/discarding the gloves afterward.
3. Putting a condom over any toy that you're about to insert into your partner's anus (note: this is something that's a good idea just in general for any toy that cannot be sterilized, regardless of your personal cleanliness preferences).
4. Using a condom, whether or not it is needed for safer sex reasons.
5. Using a sheet of saran wrap (perhaps with a bit of water-based lube on your partner's side of the barrier) to cover the anus if you'll be engaging in rimming (i.e. stimulating the external part of your partner's anus with your tongue).

2.3.2.3.2.2 Different Ways People Do It

2.3.2.3.2.2.1 With Their Partner's Fingers

Fingers are endlessly versatile when it comes to sex, and anal play is no exception. Here are just a few examples:

1. A lubed finger is an easy way to stimulate and tease the exterior of the anus.
2. A soapy finger in the shower, or a lubed finger around the behind during oral sex, are easy ways to start experimenting with anal penetration.
3. Fingers are also one of the easiest ways for men to experience prostate stimulation: once you're aroused, if your partner presses towards the root of your penis from inside your anus, then they'll probably be able to feel the gland itself (and if not you could certainly tell them once things start to feel interesting).

One important point: fingernails should be short if you're going to use them for anal penetration. Remember that the tissues of the anus are extremely sensitive, so any bumps or sharp edges to your fingernails, even if they look small, are best avoided.

2.3.2.3.2.2.2 With Their Partner's Penis

Fingers and/or toys are actually the best way to get started with anal penetration, but for some people who have male partners the thought of penetration by their partner's penis may be a potent one.

Lube is always in order, as are condoms (particularly if there are any possible STD concerns, or if one of you has concerns about cleanliness).

It's also especially important for the penetrating partner to listen: if your partner asks you to slow down or stop, and you don't listen, then at a minimum you're risking spoiling this activity for the two of you in the future.

2.3.2.3.2.2.3 With a Sex Toy

The big safety virtue of toys specifically designed for anal play is that they can't get ``lost'' inside the anal passageway, no matter what kind of mishap may happen: they generally have flanged bases which prevent anything like this from happening.

And, of course, they're given shapes meant to feel good --- perhaps involving small bulges that provide a fascinating sensation as they slip past the anus itself.

2.3.2.3.2.2.3.1 Butt Plugs

For most couples (or individuals who simply want to add a new dimension to masturbation), the simple ``butt plug'' will be just about the ultimate anal toy: not only are they designed not to go too far in, but they're also designed to easily stay in without anyone's hand there to keep them in. So, you can put a condom over one, apply some lube, insert it, and then go on having sex the way you normally do, but with the addition of an interesting new sensation in your pelvic area that accompanies every pelvic thrust, PC muscle squeeze, or orgasmic contraction.

2.3.2.3.2.2.3.2 Anal Dildos

The distinction between these toys and butt plugs is that anal dildos aren't meant to stay in on their own once they're inserted: rather, they're intended to be slowly thrust in and out, by either you or your partner, for a sensation of movement within the anus that's quite distinct from the insistent/consistent pressure of the ``stay in place'' butt plug.

2.3.2.3.2.2.3.3 Strap-On

A strap-on harness allows one to hold an anal dildo in place against the pubic bone, hence allowing ``hands free'' anal penetration. Although in theory there are some circumstances in which men might choose to wear a strap-on (perhaps using a different harness design that holds the dildo against the upper thigh rather than against the public bone above the penis), in practice these toys are mainly purchased and worn by women for use with their partners.

2.3.2.4 Everything Else

This section covers several popular forms of sex that are just a little less common than most of the ones we've discussed so far.

Personally, at least when it comes to anything safe, I feel there's a lot to be said for cultivating a mutual ``Sure, why not? Let's give it a try and see if we like it...'' attitude:

1. When it comes to kinds of sex other than the ones you and your partner usually have, you'll probably have to communicate at least a little bit just to make the new thing work. This may make communication easier even for the kinds of sex you usually have --- and never forget what a big difference it can make if you're able to say ``Mmmm... Just a little more to the left...'' or ``Just a little softer, sweetie'' or ``Oh wow keep doing exactly that'' or ``God yes, fuck me harder!'' to your partner and then get what you're asking for.
2. Life often seems to go by more quickly than we'd like. If there's anything you and your partner might enjoy together beyond what you're currently doing, then it's probably better to find that out sooner rather than later so that you have even more years to enjoy it together.

2.3.2.4.1 Role Playing

``Role Playing,'' for example where one partner agrees to be ``in charge'' of what happens during sex that evening while the other partner agrees to assume a submissive role, or where one partner agrees to play the role of the pillaging rogue while the other plays the role of the fair maiden, is a very popular and perhaps even beneficial kind of sex play:

1. In its ``power play'' or ``Dominance and submission'' forms (i.e. where one partner agrees to do what the other tells them for a certain period of time) it can serve as good practice for the ``dominant'' partner in learning to communicate about what they want sexually, while the ``submissive'' partner may get to enjoy a brief respite from the stress of having to make decisions.
2. In the case of other kinds of roles it can serve as a creative outlet, as well as an erotic opportunity to experience your partner acting and dressing like a completely different person --- perhaps almost like having an affair without having an affair?

Either way, it's important to keep in mind that the following principle should infuse any form of role playing, just as it should infuse any other form of sex with your partner: ongoing consent. In other words, any of the people participating in the role playing ``scene'' should be able to stop it at any time, and there should be a way to easily distinguish acted-out pleading in the context of the scene (e.g. ``Oh no Mr. Pirate please don't put that in me it's so big!!!'') from a real request to slow down or stop (e.g. ``OK, this is seriously not working for me, we need to stop right now.'') Generally, the clearest way to be sure there are no misunderstandings is to pick a ``safeword'': an unusual word or phrase like ``red'' or ``safeword'' or your partner's middle name, which when used by either of you means you both stop what you're doing and either quit for the evening, take a rest break, or discuss/resolve what was going wrong and resume.

2.3.2.4.1.1 Discovering Your Fantasies

Figuring out what kinds of fantasies you or your partner have (and ideally have in common) is a good first step, so that you can make an initial guess as to what kinds of roles might be fun to play out with each other. There are two general approaches to finding them: the ``on your own'' approach and the ``with your partner'' approach.

Of course, there's no reason you can't try both.

2.3.2.4.1.1.1 On Your Own: Thinking Back on Your Best Experiences

Personally, I'm of the opinion that we have more to learn from our best sexual experiences than from our worst ones. So, which do you consider your best sexual experiences? Is there anything they all have in common?

Alternatively, what scenarios do you fantasize about when you masturbate? If you're not used to fantasizing when you masturbate, then at least try to imagine some of the common sexual activities and fantasies you may have at heard about, in the hopes of finding something that's an obvious hot button for you.

At this point we should probably pause to address ``fantasy vs. reality.'' In general, fantasies can be strange things. Personally, I have erotic fantasies involving being crowned emperor with complete dominion over the entire earth. Yet, ironically, in real life I have no serious attraction to a career in politics, and in general can see no relation between this fantasy and what I actually do (or even want to do) in real life. Nevertheless, my fantasy is no less potent for this.

In other words, it is your actions in the real world which matter: as long as you're sane and can distinguish between ``fantasy'' and ``reality'' as easily as you can distinguish between ``fiction'' and ``non-fiction,'' then I personally wouldn't worry too much about the level of ``political correctness'' in your fantasies. And, if you and your similarly consenting adult partner can find a way to act out something like them in a safe way that involves only each other, then more power to you.

2.3.2.4.1.1.2 With Your Partner: ``Keep Talking or I'll Stop''

Ah yes... The classic game called ``Keep Talking or I'll Stop.''

You could probably figure out how it's played just from the name, but the general idea is for you to give your partner his or her favorite sexual act, and as long as he or she continues to stream-of-consciousness babble