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Pegging is a term coined by the audience of Dan Savage's audience, a sex columnist and educator. Pegging is not about anatomy or sexual orientation, it's focus is on gender. It's when someone who identifies as a man is anally penetrated with a dildo by someone who identifies as a woman. This is why you will hear me say man, woman, he, she etc. when I typically don't.

Here are some other resources on pegging:
http://pegging101.com/
https://www.neogaf.com/threads/pegging-101-your-guide-to-girl-dick-on-man-butt-interactions.1274158/
https://jezebel.com/5782240/everything-you-need-to-know-about-pegging
https://www.thestranger.com/seattle/SavageLove?oid=7730


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This episode of Sexplanations is sponsored by Adamandeve.com, a strap on super store. When a woman uses a strap on to have anal sex with a man it's called pegging. To me pegging is a sex act that makes a lot of sense. Typically men can have stronger orgasms from prostate stimulation, and the prostate is most easily accessed through the rectum.

Pegging can also be really pleasurable for the woman to express fucking as the penetrative partner. Curious about pegging? Want to know how to incorporate pegging into your sex life? First there's bringing it up with your partner. You might say something like: "Sexplanations has this video I'd like to watch with you." "How do you feel about me doing you in the ass?" "Are you into exploring prostate massage?" "I'd really like to penetrate you from behind while you stroke your cock." "I want to fuck the cum out of you." 

There are also some test behaviors you can try; dry-humping from behind in the kitchen, or the shower, or the bed. Pressing gently on the perineum during a handjob, or blowjob to tease the prostate. A consensual finger in the ass, or full on anilingus. Even while eating ass, check in, "Does that feel good?" 

More than likely it feels amazing, but fear gets in the way of relaxing into it. Fear of pooping, or poop on the toy when it comes out. Fear of pain. Fear of farting, the smells in general, potential tearing, hemorrhoids, getting the bed messy, fluids, pegging failure, disappointment, giving up, or liking it too much that you need it from now on just to get off.

These fears are sexual fears. They apply to many, many sex acts. Fluids, pain, sex performance, at least with pegging there are clear steps to mitigate these fears. The first is understanding the asshole. The anus has two sphincters, an external sphincter that can be constricted or relaxed like your mouth, and an internal sphincter that is controlled by the autonomic nervous system, so it functions on its own like your heart. 

The prostate or what comedian Ali Wong calls, "The magical clit in his butt hole" is about two inches in on the anterior wall. Everything around it is the rectum. Work with the anatomy, put a glove on your finger and find your way around. When does the asshole open up? How much pressure is desired? Where is the prostate? Does your partner want rapid strokes, long strokes, deep strokes, tickling, or no movement just touch? 

For more information and general guidelines on anal prep and anal sex, check out the videos in the description. The next step for pegging specifically is securing a strap on. That means a dildo and some way of attaching it to your body so you can thrust hands free. Traditionally this refers to a harness with adjustable straps, and an o-ring that the dildo can slide in and out of, but there are also underwear versions.Sspecial night rhinestones, and this style called a U strap that makes your vagina the o-ring. This one has a vibrator so the crotch becomes a three-way pleasure factory.

My recommendation is that the dildo be the size of the person's bowel movements. Small squirts, something like this. Big dumps, you can go larger. This kit is nice because it offers both options so that you can work up to a heftier girth over time. Then there's these very reasonable sizes with two colors to choose from, your anus, my anus. Dildo for anal, dildo for vaginal. A longer phallus is nice so that you can really get in there and don't have to worry about easily slipping out. There's enough room here for buttcheeks. 

Materials do matter but I wouldn't spend a ton of money on your first strap on. Make sure you like pegging before a big investment. You're going to use condoms to keep things safer and cleaner anyway, right? Harness wise I like having something adjustable that can be washed, but these were really fun to wear in the orgasmic sex positions video. Once you have your gear selected; dildo, harness, lube, condoms, baby wipes for clean up, and toy cleaner, set a date. 

Personally I'm a big fan of hotels for anal. It's not about disrespecting the hospitality industry, it's about keeping body fluids separate. There are usually two beds in a room, so you can designate one for ass adventuring and the other for all other kinds of sex and sleeping. If you're going to do it at home, I suggest aiming for the evening prior to laundry day. It's unlikely that there will be visible feces to clean up, but there will be E Coli that gets moved around.

And some forethought is wise; like taking showers first, not pegging after a meal with beans, and probably not when there are other people around so your "put it deeper in my ass" can be communicated clearly. Next workout a back up plan for when things don't go smoothly. It might if you don't take it easy or use proper gear. Your brain might get in the way, all sorts of lingering sex shaming, religious, or social beliefs that tell your butt to stop. 

Knowing that you could switch to oral sex, or mutual masturbation, or cuddling with hygiene considerations of course can make those full stops less disappointing. Now onto pegging. With the strap on in place, get the man aroused; handjob, blowjob, masturbation, vaginal sex. He may not get hard, or stay hard, but it helps to bring blood into the groin and start things off pleasurably.

Get into a position where he can maintain stimulation, and you can eventually thrust the dildo inside him. Position. Position. Position. Position. According to proctologists standing with feet pointed inward can open the anus more, so can spreading the butt-cheeks. With a lubricated condom on the toy and some extra lube for good measure, introduce the tip to his anus. Just wait it may pucker up and draw you inside. If not when you and your partner are ready, push slowly and steadily listening for directions. 

"In more, slower, up higher, right there." A strong rub of the prostate, while thrusting slightly slower than how he strokes his penis is a good starting move, but if it's not working get into a position where he has more control, and let him lead the pegging. Position. Position. Position. You're wielding a appendage that's not connected to your nervous system like an actual penis. 

It cannot give you complete feedback about the other person's asshole, so things might be awkward; they might be tiring because you're working a new muscle group. Listen, ask questions, and stop if it hurts! The last thing you want to do is damage the fragile tissue needed for regular bowel movements, or condition the body to associate pegging with pain. 
 
It's possible to orgasm from pegging, pegging and being pegged. It can improve your relationship dynamics, refine your communication skills, and enhance your sex life. Slow, steady, and smart. Stay curious. All of these strap ons are from Adam & Eve. You can get them and many other products like condoms, lube, sex cushions, and sex swings on their website AdamandEve.comThey'll give you 50% off of an eligible item in your shopping cart if you use the discount code DOE, plus free shipping in the US and Canada.