On a warm August night last year at my favorite inn on the north side of town, I gave my new FWB McDaddy a proper buggering for the first time.
McDaddy, just separated from his wife, had recently achieved silver fox status in my eyes due to some cosmetic improvements and was really starting to enrapture me. Yes, OK, he was still in a state of long-term unemployment. And yes, he was temporarily homeless too. But hey, at least he looked good, had weeknight availability and was adventurous too! I wasn’t in the market for a husband after all, just a fun fuckboy.
And fortunately for me this particular fuckboy was down for some pegging.
I was pretty amped because 1) I find pegging to be empowering AF and 2) I already owned a designer harness that I’d used on just one other person at that point.
My harness was shimmery and sliver and had a fur lined interior. I’d bought it at a sex shop in D.C. so whenever I wore it, I felt like a leader of the free world understandably. And I was especially excited to see how it would look with the hot pink dildo McDaddy had brought with him that trip.
“Pinkie” as we dubbed the dildo, was a girthy, respectable 6-7.” She was quite pretty.
I was kinda impressed McDaddy was ready for something that substantial based on his limited previous experience.
But McDaddy trusted me with his bum and even through he was shuffling a few “girlfriends” at the moment (again, unemployed), he assured me I was the one that “owned his ass” and that what we had was “truly special.”
I mean, who cares if he was love bombing me, owning someone’s ass was totally flattering! Therefore, I was bound and determined to love bomb me some McDaddy booty that night.
So, he proceeded to get Pinkie all snapped into the O ring of my harness, as I set the mood by dimming the lights and playing some adult contemporary rock music on my phone.
It was time for me to suit up. I stepped into the harness, pulled it up and tightened the straps to the point where they were digging into my skin. I’d learned from earlier experiences that the straps tend to loosen easily when thrusting hard and fast, so this was an essential rigging step.
I grabbed my We Vibe, powered it on and placed it inside of me, hoping the harness would stay tight enough to keep it in during action.
I lubed up Pinkie good (this time with commercial product, not the organic variety I sometimes use on him) and instructed McDaddy to lay on his back. I wanted to fuck him in missionary position to leverage his body weight and stare directly into his eyes as I was penetrating him.
I crawled to him on the bed, lifted his thick legs over my shoulders and slowly guided Pinkie into his love canal. Pretty quickly I could tell from the look on his face that there was some discomfort.
I’d stop every inch into his ass to make sure he was still breathing.
“You OK? You want me to keep going?”
He repeatedly nodded yes. I don’t think he was capable of spoken words at that point.
Once I got Pinkie “balls deep” in his ass (the quotes because Pinkie didn’t have balls), I let him breath for a few seconds and settle into the sensation.
Then I leaned over his face and started kissing him hard and passionately.
With my vibe in, the kissing felt incredible and I naturally started pumping my pelvis in a continuous fucking motion.
We moved his legs up behind his head which provided the most direct and deepest access and allowed me to sync into a nice rhythm.
I had total control over him. I’ll never forget that completely vulnerable look in his eyes that night. I tried to smile and kiss him often to make the experience feel more sensual and less sadistic.
We weren’t making our usual sounds, just taking in the music playing in the background.
I could tell he was focusing on the p spot stimulation since he wasn’t hard. I asked if he wanted to stroke himself while I was inside of him and he didn’t seem interested.
Not surprisingly, my vibe managed to slide out at some point while I was making sweet love to him. But it didn’t lessen the experience as I was still very much enjoying the connectedness I felt in the moment.
I don’t recall how long the pegging session lasted. When he decided he’d had enough, I gracefully pulled out and retreated directly to the dark bathroom to remove the entire harness system and drop it in the sink under hot water.
“Don’t worry, I’m not looking!” I assured him a couple times to reduce his ick factor anxiety.
When I jumped back in the bed, we high fived and I got the the signature McDaddy compliment, “Good job Team!”
Being his Quarterback was fun.
Source: reddit.com/r/gonewildstories/comments/10z0xxl/fm_drilling_mcdaddy_a_pegging_tale