I love my butch and would like to oblige this fantasy, but I’m stumped. I have no idea what to do.

Dear Fairy Butch: My partner and I have been together for almost 10 years, which seems incredible since we’re both in our early 30s. We have a very satisfying sex life, but I have one issue. My partner has a fantasy that she’d like me to fulfil. She’d love for me to give her a blowjob while she wears a strap-on. She tells me it’s about the role-playing aspect and she’d love to know how it feels. I love my butch and would like to oblige this fantasy, but I’m stumped. I have no idea what to do. She was my first sexual experience ever, which she knows. What would be the best way to do this for her without coming off as looking, or feeling, ridiculous and stupid? — Loving Partner in Pittsburgh

Dear Love: Darling, the key to giving an awesome strap-on blowjob lies as much between the eyes as it does between the thighs. It’s no wonder you might feel timid at first—not only do you lack experience, but the sometimes mystical act of strap-on cocksucking can be rather confounding to some. But even though you won’t be simulating a flesh and blood cock, you can still engage her physically. Why does she want you to perform this feat for her? In addition to the actual physical sensations a strap-on blowjob can elicit, the imagery involved—you perhaps kneeling before her, stroking her thighs with her cock bobbing in and out of your mouth—can be quite powerful and pleasurable indeed.

In my book, The Ultimate Guide to Strap-On Sex: A Complete Resource for Women and Men, I devote a chapter to finding the “inner dick,” and dildo fellatio is an especially good time for both of you to envision that hunk of silicone or PVC as a material expression of psychic reality. For those minutes or hours in which you’ll be involved in the endeavour, do what you can to envision the piece as her real cock. This works best, by the way, with a realistic dildo, complete with head, shaft, veins and balls.

Make sure that the base of the dildo is solidly connected to your lover’s vulva. Use your lips and tongue to caress the head of the cock, lick the shaft, grab the base and tap it against your lips and face. Do all the things that you think might feel good, including licking the underside of the shaft, tonguing the balls and kissing the head gently. When you really start to get going, suck the head as you stroke the shaft rhythmically and press the base into her pussy. This is where the visual and the physical sensations of the act really come together! Your butch may enjoy a finger or two in her vagina or anus, though she may well prefer them left alone in order to preserve the fantasy of altering her gender.

Here’s to your first blowjob, my dear. May you and your partner enjoy it in good health!

Dear Fairy Butch: I am engaged to enter into a long-term commitment (via nuptial ceremony) with my lover of nine months and we are planning to continue with our monogamous relationship. I am in my early 30s and she is in her mid-40s. One issue that we expect to be facing soon is her menopause. I am curious about what effects that might have on our sex life. — Connoisseur of Older Women in Connecticut

Dear Connoisseur: Well, sugarplum, I’m not going to lie to you: Certain changes affecting sexuality do occur in postmenopausal women. Yet there are remedies as well as ways of relating to these changes. First, let’s get to the changes that occur in some women. These are: a) vaginal dryness and thinning of the vaginal lining b) lessening of the libido, and c) less intense orgasms and the need for increased stimulation in order to get to orgasm.

Now, let’s get to those remedies. Vaginal dryness can be readily dealt with through the application of Astroglide or K-Y Jelly, and local estrogen creams can decrease vaginal thinning without influencing hormone levels throughout the body. If juicing things up doesn’t solve the issue, systemic estrogens in the form of pills and patches can be used. The lowest effective dose should be used and progesterone can be added to protect the uterus. Small amounts of testosterone can often boost a woman’s flagging libido and orgasmic intensity.

Attitudes can be restructured to accommodate postmenopausal women’s changing bodies. Some folks find the extra time and attention required to reach orgasm a great time to cuddle and connect with their partners. Also, many women really come into their own at the time of menopause, having developed increased sexual skill and confidence, as well as a greater sense of emotional security. For more info, check out thirdage.com