From pain to pleasure


Dear Dr. Jenni,

I’ve been with my boyfriend for a little over a year, but intercourse has always been painful for us. Once he is inside, I tend to relax and intercourse becomes easier and more pleasurable, but getting inside is such a struggle for us. I find that I close down and get very anxious. How can I make this process easier and less painful?

—Painful Penetration

Dear Painful,

It sounds like you carry some tension around sex. The secret is to find a place of peace and relaxation earlier in the game. I’m curious about what is happening in the desire and arousal departments before you get to intercourse? Is your brain sufficiently turned on (aka desire)? Is your entire body excited and throbbing with pleasure (aka arousal)? Are there any ghosts in the bedroom that might need to be cleared out in therapy?

It’s important to have these elements in place before jumping to the main dish. However, it would also help to have your boyfriend team up with you to tackle this issue. Together you can play a game where you pretend sexual activity is an art. Consider your vulva as a canvas and his penis as a paintbrush. As you lie on the bed, imagine yourself melting into the mattress. Use breath and muscle relaxation exercises to help you further let go. Have your boyfriend take his penis and lightly caress your vulva as if he is painting a masterpiece. He can trace your inner and outer labia, your clitoral hood and clitoris, and slowly dip the tip of his penis into you, very slowly, as you guide him in when you are ready.

The more flaccid he can be, the better, but if he is too aroused and erect, that is fine, too. The idea is for him to be soft and sensual and for you to be able to fully open and relax so that the initial penetration is not painful or tense.

Keep in mind that that sex includes more than just intercourse. Don’t force an activity if you are feeling pain or tension. Sex is about pleasure, and there are a plethora of other sensual and fun activities to enjoy.

Dear Dr. Jenni,

I’m a recently single, gay male who has been in a monogamous relationship for the past 25 years. I’m a little afraid to date again because of the  onslaught of STDs out there. I’m curious what are the chances of getting HIV from oral sex, specifically with regards to blow jobs?

—Daunted by Dating

Dear Daunted,

HIV can be contracted when infected blood, semen, vaginal fluids or breast milk enter the bloodstream of another person. Thus, chances of contracting HIV from oral sex are significantly lower than vaginal or anal sex because the degree of HIV in saliva is minimal. This does not mean zero risk. Research shows that the giver in oral sex is often more susceptible to HIV, particularly if there are irritations or cuts in the mouth, or recent dental work.

Furthermore, unprotected oral sex still leaves the possible risk of other STDs such as herpes, gonorrhea and syphilis. I highly suggest using a condom with oral sex to help prevent any STD, but if you do forgo the condom, at least make sure your partner ejaculates outside the mouth to further decrease any risk.

Enjoy dating but remember that safe is the new sexy, and condoms, especially flavored ones, can make an oral sex experience “mind-blowing.”

Send questions for Jenni Skyler, Ph.D., to Skyler is a sex therapist and board-certified sexologist who runs The Intimacy Institute in Boulder,