The act of pegging entered my consciousness in the late 90s with the release of Bend Over Boyfriend by Shar Rednour. It was so deviant. So transgressive. I wanted in! (Pun so intended.) Picturing myself bending Flick over our bed and fucking him, I even went to the local feminist sex toy store and bought myself a lovely leather harness. I figured we’d pick out the dildo together.
Flick was alas, not so interested in taking a dildo up the ass, despite enjoying my tongue and finger.
“But your prostate…” I argued. He was not convinced.
Fast forward approximately 17 years and I was finally able to take that optimistically & prematurely purchased harness for a spin, first with a few women, but eventually for its intended deviant purpose. Woo hoo!
Non-monogamy opened so many avenues for us (goddamn it, there’s no way to write about this without endless innuendoes) and as Flick got more and more comfortable in a community that celebrated and valued men who stepped out of their traditional role of penetrator and were willing to be penetrated as well, he decided he was open to it after all (heh, open–last one, I promise). He’s admitted that initially he agreed to trying it because he knew how into the idea I was, but the more experienced he got with butt play and began watching hot pegging porn, the more into it he got for his own pleasure.
We started slowly and it took us many months to move beyond tongue/finger/small plug to fingers plural and larger plugs. The ‘beginner’ dildo (Mistress by Vixen Creations) recommended by Tristan Taormino intimidated him so I got a smaller one (Nova by Fuze) and we gradually worked up to getting it inside him guided by first his and then my hand.
Our first attempt at pegging was during a threesome with Hot Mama. He’d gotten us both off several times and I’d warmed him up with several fingers. Walking back to the bed after strapping on, I caught my first ever glimpse of myself in the mirror with a harness & cock. Damn! I looked so fucking hot! Flick and Hot Mama agreed and joined me at the mirror to stroke me as we took in the sight.
Flick dropped to his knees and began to fellate me and if it were possible to die of hotness both Hot Mama and I would have dropped dead on the spot. I couldn’t actually feel his mouth, but fuck, could I ever feel his mouth. When we were ready, he bent over the bed and I was able to get inside him. Hot Mama’s mouth on his cock convinced him that this was a very good thing and we were able to enjoy it for several minutes until I got a little enthusiastic and thrusty and he had to call it.
Flick doesn’t actually enjoy direct pressure stimulation of his prostate so angle is a piece of the puzzle we hadn’t considered. He played a bunch solo after our first attempt and worked up to enjoying the Vixen dong so we decided to try again, this time with him riding me so he could control speed and depth. We started slowly with me not moving until he was ready and he came so hard he hit me in the eye (thankfully closed in time) and sprayed the pillow next to my head.
I have to say that him straddling me and panting and sweating while fucking himself on my cock is the hottest visual. It is a regular go-to in my spank bank and our sexy friend Bex was so overwhelmed by the hotness watching us during a repeat performance that she shook uncontrollably for about 5 minutes.
It’s not a frequent act in our repertoire but it is something we’ve both come to really enjoy. We celebrated International Women’s Day Deadpool-style with him riding me during a threesome with Iris and both she and I loving every subversive minute, both moaning aloud when he demanded, “Fuck me!” I’m thrilled that it is something we can share that feels especially intimate due to his vulnerability in the act, and the partners we’ve shared it would all enthusiastically agree.
Plus, if I ever meet any feminist heroes, like Abbi on Broad City, I can proudly exclaim, “I pegged!”
