Click here to enter and win a free copy of Welcome to the Club: A young man discovers the joy of prostate play. How cool: A new way to orgasm! But if playing with a plastic dildo is fun, what about the real thing? A real cock probing and rubbing his gland? He’s not gay, which is a problem. He sees an ad in an alternative newspaper: “Open membership/Exclusive men’s club/For the adventurous.” A few phone calls later, he’s on the way to an upscale hotel for his initiation into a very special club for men who are straight, professional, “and enjoy the Greek side of things.” His initiation will be an evening of sex and submission to six experienced men. [M/M, anal sex, serial gang bang, gay gang bang, masturbation, fellatio, oral sex]
I spent a lot of time shopping online: masturbation sleeves, vibrators, hand job creams, artificial pussies… And I stopped being shy about subscribing to porn sites. From now on, it was premium only.
On a whim, I bought a dildo.
It was in the bottom of the box of the latest delivery. For deep psychological reasons I’ll never uncover, I had clicked on “eight inch” in the drop-down box. One thing’s for sure, it was bigger than my cock.
What to do with it? Then I remembered something I read about the prostate gland, located at the base of the penis and only accessible through the wall of the rectum—something about how direct stimulation could trigger an orgasm.
I’d fingered myself, and it didn’t work. Maybe a contortionist could do it, but not me. This dildo might be the ticket to a new kind of orgasm.
Then I had another brilliant idea: How about the electric vibrator my not-belated ex-girlfriend left behind?
I put a pillow in the middle of the bed, covered it with a clean towel, and plopped my ass down, the lube, dildo, and vibrator close at hand. I even rigged up a mirror so I could watch the fake cock slide into my ass. In hindsight—bad pun, sorry—I should have recorded my inaugural ass-fucking masturbation session on my smart phone.
My virgin asshole was tight. It took a few minutes of gentle probing, but I finally managed to stretch the taut little opening of my ass. With a thrust, it was in. After the burn subsided, the sensation of penetration and fullness was pleasurable. I was tentative, not plunging too deep, and not very fast. I got the dildo in about four inches and held it.
I put the vibrator against the base of the artificial cock, the power on low. The vibrations traveled up the length of the dildo to the head, now pushing against my prostate.
Holy shit! It was an entirely new sensation from an erogenous zone I didn’t know I had. Something glowed deep in my pelvis, building toward an orgasm. I held the vibrator against the dildo as my cock got harder and harder. As the pressure mounted, I watched something I’d never seen before.
First a trail of clear liquid trickled out of my dick. Pre-cum, that I’d seen before. But this was new: Jism flooded out of my cock, which was standing up on its own, untouched by my hands, twitching and throbbing.
My cock was fully erect, my balls scrunched up against the base, and throbbing from the relentless vibrations on my prostate gland and the fullness of the dildo inside me. A stream of white jism dribbled out of my dickhead and ran down the shaft, pooling on my belly. I made a big mess.
For sure, it wasn’t an explosive orgasm, like from thrusting or stroking. This orgasm was completely different, but still satisfying. After cleaning up and putting the sex toys away, I did more online research. Turns out, what I just did is called prostate milking.
Gee, twenty-eight years old and I learned something new about my body.
I worked prostate play into my masturbation routine. Over the weeks, my asshole adjusted to the girth of the dildo. I also rigged the toy in the bathroom, using the suction cup base so that I could fuck myself in the ass and watch in the mirror.
You can see where I’m going here, right? If a dildo is good, what about the real thing? What would it feel like to have a hot, stiff prick plunging into my rectum and wreaking havoc on my insides?
Word count: 6,100
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