When I was leading a workshop at a conference recently, I received the following question from a participant. “I have been with my boyfriend for one year. We are both virgins. We’re talking about having sex, but I’m not sure. How do you know when you’re ready?” The question of whether or not you’re ready for sexual...

I think I'm having an affair with my prostitute. For the past two years, I have been seeing a prostitute twice a month. I'm single and really don't date under normal circumstances. During the past month, we have been talking more and seeing each other outside of our business...

The term “fisting” refers to the practice of inserting the entire hand into a partner’s vagina or anus. In the gay community, this is often called “handballing,” which I consider a more accurate and less frightening term. When people hear the word “fist,” they often imagine something violent, as if you’re going to be punching someone’s genitals. This is not the case...

Last week, I facilitated a sexuality education workshop for a group of college students, which I ended, as usual, by collecting and answering anonymous questions. I asked students to write either a question or their favorite sex fact on an index card, with the goal being to collect a card from everyone regardless of whether...

When people talk about "actual sex," they are usually referring to penis-in-vagina intercourse. As countless sex educators have written, the majority of women don't get enough clitoral stimulation from this type of sex alone to have an orgasm. Part of the problem that many people have is that vaginal...

I am a female in my 20s who has a boyfriend close to my age. We have been together three years. I am able to have multiple orgasms with a vibrator (a plug-in style) that I use on myself, but I have never been able to give myself an orgasm with my fingers alone. My big problem is that while I can orgasm by using this vibrator on myself...

Last weekend, we held a "Strap-On Sex 101" class at the Tool Shed. This was the first time that we had offered this particular workshop, and I was fascinated to see that it generated more phone and e-mail inquiries than any other class we've held. Many people wanted more information about exactly what would be covered during the...

This week, my friend Gwendolyn Glover has asked me to guest-blog on her Web site, Little Miss Writer. Her theme for this month is people's relationships to their bodies, and she asked me to write about how I think a person's body image affects their capacity for sexual pleasure. I'm cross-posting my thoughts here and on Gwendolyn's blog...

This column is written in response to a suggestion from a Tool Shed customer who felt that talking with us at the store had made him feel less "weird" (his word) about his desires, and thought that other men might find the same information valuable. So, forthwith: a beginner's guide for heterosexual men who are interested in being anally penetrated by their female partners...

In my mind, there are two separate questions being asked here. The first is about female ejaculation, and the second is about incorporating urine into erotic play, which is often called watersports or piss play. It is likely that the clear fluid that you saw was female ejaculate, which sometimes appears when a woman's G-spot is stimulated. Many sex educators...

I’m more curious about non-pharmaceutical aids. The stimulating gels [that were mentioned in the last column] would fall into that category, but what about aphrodisiacs, supplements, etc.? Big Pharma gave people this problem in the first place! If someone can’t afford yet another single-source name brand [prescription drug...

I have a wart on my penis that has been there for about 15 years. It is getting larger, about 10 millimeters, currently. I have been monogamous with my partner for 20 years. Three questions: Can this wart be removed? Can I infect my partner? Will a condom prevent infection?

A common side effect of many antidepressants in the SSRI (selective serotonin reuptake inhibitor) class is “sexual side effects” in both men and women. These include decreased libido and anorgasmia. Are there any remedies that don’t interfere with SSRIs and birth control that can relieve these unpleasant side effects?

At this time of year, we get many people in the store who are looking to purchase presents for their partners. Buying a sexy toy, book or DVD for someone can be a great way to spice up your relationship or carve out some me-time during the crazy holiday season, but since every person's sexual desires and responses are so...

Some of the most frequently asked questions that we get at the Tool Shed concern sexual lubricants. Customers often stand in front of our Wall of Lube, wanting to purchase some, but unsure where to start. Sometimes they've never used lubricant before, and sometimes they've tried a lube that has irritated them and are looking...

As a sexuality educator, I believe there are many reasons for someone to choose not to engage in sexual activity. In two of my previous columns, I answered reader questions about asexuality, which is generally defined as not feeling sexual attraction or desire. Celibacy is different, as it can involve people who do have sexual desires...

For those unfamiliar with "dental" dams (so called because they were originally used during dental work), they are rectangles of latex or polyurethane that can be held against the vulva during cunnilingus or against the anus during analingus or rimming. They act as a barrier to the transmission of sexually transmitted infections (STIs). Many sexuality...

As regular readers of this column know, I get a lot of questions about oral sex and sexually transmitted infections. Since you seem to be specifically asking about HIV, I'll focus on HIV transmission during oral sex. There's an interesting history behind your question. In the United States, the HIV epidemic was initially concentrated among men who had sex with men...

I'm going to answer this question in two separate columns. To my knowledge, your friends' risk-reduction strategy of not getting semen in their mouths is an effective one, but I am going to do some more research on the level of HIV or other STIs that are present in pre-cum. Pre-seminal fluid does contain HIV...

Last month, actor and filmmaker Madison Young visited our fair city to present "Reclaiming Pornography One Orgasm at a Time," which examined the differences in and the debate about mainstream, independent and feminist pornography. After she gave this talk to a standing-room-only audience clad in nothing but her underwear...

My first job out of college was working for a nonprofit in Washington, D.C., that focused on consumer advocacy issues. One of their big campaigns while I was there involved pushing for federal regulations of dietary supplements such as vitamins. At the time, I was astonished to learn that these weren't already regulated. They contain potent ingredients that are supposed to have a significant impact...

Mark Sanford. Larry Craig. Mark Foley. Bob Allen. Michael Duvall. John Ensign. And the list goes on—Republican politicians who say one thing about marriage and homosexuality, but do quite another. Since the never-ending stream of scandals...

What are the symptoms of gonorrhea, syphilis and Chlamydia? What are the risks of giving oral to a man and receiving oral from a man? When I lead workshops on safer sex, I often ask participants to name the most common sign of a sexually transmitted infection (STI). While they usually come up with a long (and sometimes wild) litany of pox, pus and pains, this is actually a trick question...

A few weeks ago, I answered a reader question about changes that occur in women's sexuality as they get older. Men, too, experience normal fluctuations in sexual functioning with age. One of the most common changes that many men notice concerns their erections...

Do most women like having their butts licked, or is my girl special? Oral-anal contact, also called analingus or rimming, can be very pleasurable to people of all genders. The entire butt, from the cheeks to the crack to the anus itself, is one big erogenous zone for many folks. Kissing, licking...