‘Side’ and ‘Pegging’ – Wait, What?

Last year, in a conversation with a friend who is back to the dating scene, she asked me about two terms she’s noticed on some dating apps: ‘side’ and ‘pegging.’ They were foreign to me as well, so I began my research.

For ‘side,’ think of a big meal; there is a main course, then there are side dishes and desserts. With sex, if receptive/insertive vaginal and anal intercourse is the main course, then the sides are everything else. Some people no longer want to have insertive or receptive vaginal or anal intercourse.

There are myriad reasons for this. It could be due to previous lived experience, pelvic-floor dysfunction, pain, antidepressant use, medical condition or many other medical issues that make vaginal and anal intercourse impossible. Vaginal intercourse can be overrated for females, as it is estimated that only 25% of us achieve orgasm that way. Unless the female is on top or having sex doggy style, they won’t have clitoral stimulation, which is what helps with orgasm. Let’s be honest, we all want orgasms — they feel fantastic. But females don’t need vaginal intercourse to reach the height of orgasm. This is where toys come in.

Sides enjoy robust sex lives filled with satisfying orgasms, and intimacy with their partners. Think about the many of ways to achieve orgasm without intercourse: cuddling, caressing, touching, playfulness, whole-body embracing, hand massaging, digital stimulation, oral stimulation and the use of vibrators, dildos, or penis sleeves. Couples who enjoy side forms of sex enjoy the same intimacy as those engaging in intercourse. They may be even more in tune with one another. Showing one another, through masturbation, how they like to be touched and how you enjoy sex with yourself is extremely revealing and intimate.

It’s estimated that three-quarters of females need clitoral stimulation to achieve orgasm. Clitoral stimulation is easily achieved using vibrators, toys or finger play. Males do not have to be fully erect to achieve orgasm or sexual pleasure. Most people believe that if a man isn’t six-to-midnight, they are not aroused, and that is not true. After the age of forty, males’ ability to obtain an erection can be unreliable. For males with erectile dysfunction there is 30% chance that medications like Viagra will not work. But these males still enjoy the stimulation of cuddling, caressing and other body-engaging activities to stimulate the brain to release those feel-good orgasmic hormones.

If you are back in the dating pool, or in it for the first time, if you see a category for ‘side’ you’ll understand what that person means.

‘Pegging’ is a newer term for an age-old practice, receptive anal sex for males. Why do men like or find pleasure in anal sex? For starters, the biological male has a prostate gland between the bladder and penis. When stimulated, the prostate (which has millions of nerve endings) can initiate an orgasm. Males can experience sexual stimulation through receptive anal sex and achieve orgasm.

If a male likes to have receptive anal sex, that does not make them gay. There is a term in the sexual-health and prevention community called MSM, which stands for men who have sex with men. These MSM males do not identify as gay or bisexual. Men having sex with men is a behavior, not an identity.

Pegging is when a male asks a female to wear a strap-on penis and penetrate them rectally. It is a thing. Since the prostate gland is erogenous, stimulating it can increase the length and intensity of orgasm when ejaculating. Some men who engage in pegging describe the orgasms they achieve as among the most powerful they ever experienced.

Enjoying receptive anal sex has a biological component, not an orientation one. Prostate massagers have been used for years to treat prostatitis. They come in a range of sizes and shapes. Some have discovered they liked prostate play after a medical provider recommended stimulation to reduce the swelling caused by prostatitis. Men who enjoy pegging/prostate play and stimulation report experiencing uniquely powerful, full-bodied, deep orgasms. Men also report enjoying the vulnerability they experience when their female partner penetrates them. For their female partners, pegging can be very empowering too.

Anal training is needed before penetration, for safety and to reduce the fissures that can come with anal sex. Lube is important; lots of lube should be available when engaging in anal play of any kind, especially if it has been an exit-only opening. Make sure your lubricant is compatible with the toy or prosthetic you decide to use. Silicone lube doesn't work well with silicone toys, for them you want something water-based.

This is Hedda Fay reminding you that sex is variable and different for every one of us. To know what you like, you have to try different things. Use protection and get tested regularly to prevent sexually transmitted infections.