You Had Me At Strap-On
Let’s talk about pegging. I’ll go first.
When my FW serious B asked if I had ever tried pegging, I was like, “am I stupid for not knowing what that is?🤔”
As it turns out, I was not alone in my oblivion, but pegging is a fetish growing in popularity among kink lovers and the sexually curious, alike.
Before I even began to probe Google for pegging info, I realized it probably was not easy for my FWB — let’s call him Jimmy — to approach the topic with me, due to butt play generally being considered taboo in our society, so I engaged with an open mind.
Wikipedia defines pegging as a sexual act in which a woman penetrates a man’s anus with a strap-on dildo. This, of course, is not all-encompassing, but sufficient for giving you the general idea. Here is a visual. (you’re welcome)
Pegging is generally considered a hetero fetish that allows for the reversal of commonly observed gender roles. Not to mention, the anus is a direct line to the prostate, which, when stimulated, can result in seismic orgasms your guy will feel from head to toe.
The role reversal aspect intrigued me, plus I was psyched to wear a strap-on, but most importantly, I could tell Jimmy was really into it, so, without hesitation, I packed for a pegging adventure.
We made a trip to the local adult toy store to browse their member selection. I had no idea what size dildo was right for Jimmy, and he wasn’t sure what size harness I would need, so after scouring the shelves for 15 minutes or so, we settled on a practical dildo/universal harness combo option. FYI: it is much more cost-effective to shop online for sex toys. We paid $80 in-store for the kit we chose; I found the same one on Amazon for $22.
Newbie angst got the best of me on the ride back to Jimmy’s place, as I mentally prepared to bang on his back door. After we arrived, we wasted no time. He helped me assemble and adjust my new attachment. I grabbed the lube while he opened Pandora on shuffle. It was time.
Jimmy is about seven or eight inches taller than I am, so I had to assume a kneel in order to meet the doggy-style height requirements for his ass. I must admit, I completely underestimated the difficulty of aligning the pole with the hole, and the acute spacial awareness required to keep said pole in said hole while thrusting. It is not as easy as men make it seem. I was intimidated and terrified I would hurt Jimmy due to my complete lack of experience, which resulted in a rigid, rocking-chair-type motion after five minutes of me strategically trying to hit the sweet spot. Imagine a dash-mounted hula girl in a slow-moving van.
Obviously sensing my insecurity, Jimmy turned around and said, “let me ride you,” to which I replied, “thank God.”
Though I had not yet done enough smashing to work up a sweat, I was relieved to let him take control. This presented me with the opportunity to watch and learn. I thought, this should be easy, as we transitioned to: the cowboy.
I lied down, my body still tense, and Jimmy mounted me. It was so erotic watching him bounce up and down on my girl cock that it did not even occur to me I should be doing something. Naturally, and in error, I had assumed the spread eagle position, and was squeezing Jimmy between my thighs with my knees at a 90 degree angle. You could see how this might be problematic, as I was restricting his movements from the waist down. Jimmy patiently placed his hands palms-down on my knees and gently pushed down until my legs were parallel to the mattress. While impressively maintaining an erection throughout, he graciously explained that I needed to keep my legs straight and showed me how to thrust my hips upward as he came down, as if I was a trampoline, returning force.
When it finally clicked for me, I could see it in Jimmy’s face, and not too long after, I could feel it on mine when he blew a massive load that reached my cheek. Props for distance. I almost got off just hearing him moan and seeing his body nearly seize up as he came.
I was turned on, of course, but I also felt powerful, and like I had accomplished something. I was hooked.
Practice makes perfect, and we practiced pretty frequently. I learned Jimmy’s favorite position was a modified missionary style, where he lies on his back with his legs bent at the knees and resting on my shoulders, as I face him — kneeling down — and go to town.
After I began laying some regular pipe, the movements came more naturally, and the strap-on became like an extension of myself — the dick I never had.
I wanted to share my experience from a woman’s point of view, as most articles about pegging that I found online were from a man’s perspective or focused on the receiver’s experience, and it frustrated me. I’m a giver. As such, I leave you with a few tips and tricks to get the most out of tapping that ass:
• A thoughtful, cautious partner will evacuate his bowels/anal douche prior to penetration. If you are concerned, speak up.
• It is easier to let him choose the dildo, and you choose the harness. Don’t make assumptions about each other’s sizes.
• When it comes to strap-ons, simpler is better! Struggling with a lot of snaps and straps is a mood killer.
• Keep your willies clean and stored properly — this is of utmost importance, because — bacteria.
• LUBE, LUBE, LUBE!
• Start slow and easy, and let him tell you when to put the hammer down.
• Think about how you like to be fucked. How does he move his body? Mimic that shit.
• During doggy style, don’t be afraid of the reach-around.
• Girls, If you want to make sure you get yours, let him fuck you first. Trust me
• Hydrate, and prepare for a cardio workout you’ll actually enjoy!
• Did I mention lube?
