It’s been a good day, so far. My wife, who is menopausal and has lost all interest in sex, still spent a half-hour on the couch with me this morning with my dick in her hand. Licking her palm and rubbing her thumb along the sensitive skin of my frenulum. I didn’t cum, but being edged like that – her slowly stroking my cock while I lay on my back went instantly into the jack-off memory bank.
The pandemic has brought us closer in a lot of ways, just in terms of having to share the house during the day — but it has also widened the intimacy gap between us. I finally had to say to her “I’m done asking, so if you want to play, just grab my dick.”
The handjob was supposedly “round one” — but I knew her well enough to know that was extremely unlikely. Fortunately, during the pandemic, I discovered my asshole. And dildos. Big dildos.
At the end of the day, I turned to her and said: “I assume nothing else is happening tonight?” I’ve been upfront about retiring to the bedroom behind a locked door to “spend some quality time”, but she has no idea what that entails. I told her I planned to “retire early” — and that she should give me the room for about an hour and a half. Pre-cum was already leaking from the head of my dick as I locked the bedroom door.
I’m a big fan of a good clean-out, so I filled and re-filled my enema bulb five times, squirting warm relaxing water up my ass while doing kegels to move the water in a rinsing motion. Soon, I was clean and ready to go.
I love the texture of lacy underwear to the point of it being a bit of a fetish. My wife used to wear sexy lingerie, but the added pounds from childbirth and the reduced libido have ended those practices, probably forever. So, I started wearing men’s lingerie. I found an online company that has male garter belts, underwear trimmed in lace, and jockstraps that leave little to the imagination. I’m not in the best shape, but when I wear something like this and see myself in the mirror, blood rushes to my cock.
I slipped on a jockstrap with a skin-tight nylon mesh that hugs my cock and balls — with a visible seam running right down the center of my penis like the back side of a stocking. It pulls my dick up and outward in a way that feels like wearing nothing, while delivering a rush of kink. I adjust the narrow bands that run along my ass. Running a fingertip across my hole.
I take a pillowcase from a hiding spot in the closet — pulling four Mr. Hankey dildos from inside. I prep all four of them with a heating lube — using a pastry brush to spread the lube evenly and keep my fingers from being coated by the sticky mess. I put a towel on the floor where I will do most of my riding — and grab my weed vape and a bottle of poppers.
I put the smallest dildo — the first one I ordered — on the towel under me — while I squat just over the head. I hit the pipe three times and the poppers with a good ten-second sniff and then I lower myself slowly down.
It’s a Mr. Hankey’s “Seahorse” dildo, which looks like what I imagine the monster from The Shape of Water’s dick looks like. If you ride it from one side, there is a prominent vein that hits your prostate as it slides in and out. From the other side there are ribbed ridges that you feel all the way down as the toy sinks deeper. Each is a totally different sensation. This was the first dildo I ordered and it’s an “extra-small”. I remember opening the box and pulling it out — and it seemed huge at the time. It’s six and three-quarter inches of insertable length, with a circumference that starts at four inches, then widens to five and a half in the middle before reaching six and three-quarters at the base as the molded balls mash against your perineum.
When it first arrived, it felt like it was splitting my straight ass in two — as my body worked to accommodate a depth and girth I’d never experienced. Within weeks, I had learned to push out and relax, allowing it to slide in right to the base on the first try.
I put on my airpods and pull up Portishead’s first album. The slinky organs and pulsating rhythms hit me as I start to “dance” on the dildo. And almost immediately — my body convulses.
Since I’ve been playing with my ass, I’ve lost some of the need to handle my cock — those building sensations have been replaced by shivers in my hands and feet, escalating to whole body quivering, legs unconsciously flexing and releasing as the dildo plumbs my insides — fucking me harder than any purposeful in-and-out I could try for.
I now view that toy as pretty small – but it’s big enough to dilate my hole for “the big boys.” As I slide off it, a wave of shivers travels from my ass to my ears, my nipples stiffening, begging to be sucked. For some reason the sudden emptiness of my hole sets me off just as much as bottoming out on the toy. I lower my face to the carpet — sticking my ass high in the air, until my body slowly goes still.
I grab the next dildo in the sequence — a medium sized version of the same toy — the sensations are similar — but the bigger toy stretches my hole even wider as the girth settles against my prostate. This one is three and a quarter-inches longer, with a circumference nearly two inches wider all the way down — ending just shy of ten inches at its base. As I bottom out, my whole body shakes like an earthquake, as I’m overcome with a full-body tremor. I feel my consciousness flirting with blacking out. Flickers of sensation form a circuit from my asshole to my cock as pre-cum soaks the nylon material of the jockstrap.
The wide base of the toy means I can truly ride it, plunging deeper each time I sink down, with a fresh wave of shivers. The textures hit differently from different angles — so first I ride “reverse cowgirl” with it, feeling all ten inches of it moving in and out of me in a straight line — the ridges scraping against my prostate with each stroke. The shivers hit again, and I lose control of my legs. I fall on the dildo with all my weight, my hole gripping the toy as I convulse. I can actually feel the fluid moving down the length of my dick before leaking through the tip of the nylon pocket. I reach down and wind the viscous fluid around my finger — bringing it to my mouth to taste the sweetness of my juices — causing another clench to travel down my spine. An overwhelming wave that forces me to pull off the toy.
My whole body quivers. I feel my hole fluttering, as if searching for something to fill it again. I curl up on the towel, my vision traveling to my cock whipping up and down with every lurch of my body.
I want to see if this feeling can build, so I back half-way off, spinning it around while it’s still inside me for the opposite texture, and sink it eight inches deep. My eyes roll back into my head as the building climax picks up where it left off. I see-saw back and forth on it. Feeling the resistance of another inch. I rise and fall on the monster cock — bending towards the entrance of my sigmoid colon. I take another hit of the poppers and push out against the pressure — until my ass swallows the final two inches. My balls rest on the dildo’s rubber ones. The feeling of girth, of being completely filled washes over me. I rise and fall by the length of that tenth inch. Stabbing my guts with it. I feel the tidal wave coming again and reach down to grab the dildo by its base. Holding it steady as my brain and body disconnect from each other. My balls contract, hugging up tight — as I feel a surge travel to the tip of my cock — the fluid full and milky, some combination of pre-cum and piss.