AN ODE TO PEGGING

According to Dan Savage, who coined the term in 2001, pegging is “slang for a woman fucking a man in the ass with a strap-on dildo.” This delicious act was first showcased in an educational context 1998 in the Bend Over Boyfriend series starring sexologist Dr. Carol Queen and her partner, Dr. Robert Morgan Lawrence (which featured instructional information as well as live demos). Pegging most recently received mainstream attention when it was featured in a 2015 episode of Broad City and a even got a brief nod during a montage in the anti-superhero movie Deadpool in 2016. “Happy International Women’s Day!” whispered Vanessa into Wade’s ear as she tightened the straps on her strap-on.

When I tell my partners that I love pegging, they look at me incredulously. “I don’t get it,” one exclaimed, “what’s in it for you?” A couple of things, actually. It’s incredibly intimate, because it requires a high level of vulnerability and trust on the part of the receiver. I enjoy the sensation of strapping on a cock because, well, I don’t have a factory installed one.There’s something empowering about walking up to a wall of dildos and getting to choose the exact size, shape, color, and texture that you want. (Although I always suggest letting the person being penetrated choose the dimensions of the toy — it’s only fair). I also find it somewhat meditative. Proper pegging takes patience — deep breathing, lots of lube, and a willingness to do a great deal of warmup and to go as slow as the receiver needs to feel comfortable. It’s a mindfulness practice for me. Plus, as my colleague and anal sex guru Charlie Glickman likes to say, “The world will be a better place when more men take it up the ass.”

I had the unique experience of getting to peg three different men in March. Two with the assistance of cannabis products and one without. All three went exceptionally well, but I think the two that utilized cannabis went slightly better considering the receivers’ experience level. The one who was pegged without cannabis is my friend and colleague Reid Mihalko. Reid is a seasoned sex geek and is quite anally aware — he’s actually the person who taught me how to peg, and the first time I pegged him he assured me that “most other people will not be this easy.” He was, as usual, correct.

For the other two (at separate times of course, I’m only human), I did use cannabis to help optimize the process because one was brand new to the experience and the other only receives anal stimulation sporadically. I provided them both with a Foria suppository, which contains 60mg THC and 10mg CBD. This is useful because it enhances pleasure and reduces discomfort without numbing. Numbing is the opposite of what you want.. I cannot emphasize this enough. Pain exists for a reason — it’s your body telling you something is wrong. You have to be able to feel the pain so you can stop, slow down, add more lube, or whatever the situation requires. Additionally, cannabinoids are most readily absorbed through the mucosa in the rectum, making a suppository one of the most optimal delivery methods. Justin, my pegging newbie, only had a suppository but no other cannabis products. He said it helped him feel more comfortable during the experience and also drastically reduced next day soreness. The other, Steve, had a suppository and a few puffs of my high CBD pen from WVapes. He noted that he could take more pressure and intensity after using the suppository.

Here are my top pegging takeaways:

  • Warm up! Seriously. Spend at least ten minutes massaging the butt on the outside, then put a glove on, lube up, and run your finger(s) along the outside.
  • Trim your nails, make sure to buff off any calluses, and wear gloves. It makes cleanup so much easier!
  • A good beginner position is to have the penetrating partner lying on their back with the receiver straddling them. This gives the receiver all of the control and they can go at the pace that feels best for them.

Have you ever pegged or been pegged? Tell me all about it!

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