Oh My God You Filled Kenny or How To Sleep With Twinks - A Guide

“How do you do it? How do you sleep with so many hot twinks and make it look so easy?”

Well, I don’t think I really sleep with THAT many young skinny gay boys... but ok, it happens once in a while. Still, I firmly believe that if I can do it, YOU can do it. Just follow the steps.

Recently I had sex with an extremely attractive 21-year old. Here’s how it happened.

Step One: Don’t be afraid to try when you’ve got nothing to lose (and usually, you’ve got nothing to lose.)

I met Kenny several weeks ago at a party hosted by my friend J-Blo (that's short for Justin The Blogger. He wanted a nickname - and he's got one!). Kenny was one of, if not the cutest boy in the room, so I immediately asked J-Blo to introduce us. He did, I flirted for a while, bought Kenny one drink, flirted a bit more. He seemed mildly interested, but clearly was not really into me, and certainly not going home with me that night. Having lost nothing (except maybe 1 drink) I moved on. (If the boy you re pursuing shows immediate interest, skip to Step Three.)

Step Two: If at first you don’t succeed, try *once* again.

I was browsing online profiles on a popular website a few weeks after the party, and there was Kenny. In most of his photos he was shirtless, which I enjoyed. I decided to try once more. This step is open to interpretation – if he had clearly blown me off at the party, I would not have contacted him again. But because he was mildly interested, I jumped back to step 1 – nothing to lose.

I complimented his pictures. Within minutes, he wrote back. Sometimes, a 2nd try is all it takes.

Step Three: Once you have their attention, be fun and conversational, but be direct.

I complimented his photos, made a joke about dating websites, and commented on the freezing weather. He thanked me, lol’ed at the joke, and agreed about the weather, saying he was so cold in his dorm (!) at that moment. I told him he had an open invitation to warm up at my place with a cup of tea. He found the idea of afternoon tea so charming that 3 emails later he was on his way to my apartment.

The next step risks making me sound like a psycho killer, or more like someone who should be featured on “To Catch A Predator.” But really, think about where the vast majority of dates take place: bars. Why? Because alcohol is a social lubricant. Everyone is happier, easier to get along with, and a little bit more fun when they’re drinking.

Step Four: Add booze.

If following these instructions while at a bar, this is where you would simply buy your boy a drink. In the case of Kenny, I adapted. He arrived at my apartment for afternoon tea, announcing, “I brought scones!” (Super cute – major points for him.)

I asked, “Would you like to add some whiskey to our tea, and turn them into Hot Toddies?”

He readily agreed. We spent the next hour drinking, chatting, drinking, giggling, and drinking.

Step Five: Find an excuse to get him to the bedroom.

Had we been in a bar, this would be Find an excuse to get him to your place. I find that keeping a somewhat stocked home bar always helps, as in “How about we go to my place for a free drink next?” usually works well. In this case, already in my apartment, I suggested he look at the pictures from my recent cruise on the laptop on my bedroom. He didn’t once suggest I bring the laptop to the living room.

Step Six: Get him naked.

Depending on the boy, this step may be unnecessary – some are stripping down the moment they enter the door. In Kenny’s case it required a bit more finessing. While looking at pictures on my screen, we went back to discussing his online profile pictures, which I insisted needed to include some pictures of his cute butt. He tried arguing that it wasn’t cute, and so while he was laying on his stomach on my bed, I grabbed my camera and snapped a few quick shots. He looked at the digital screen.

“Hey, those are pretty good,” he admitted.

“They’ll be even better without your jeans,” I replied.

He paused, and I could sense this was the moment of truth. The he said: “Well, I am wearing really cute underwear.”

He slid his jeans off and went back to lying on this stomach and looking at my laptop, while I took some more shots of his ass in his tiny boy briefs. Then, knowing he was past the point of protest, I slid the briefs down to expose he pert little butt, and snapped a few more. I showed him the camera. He approved. Then, I straddled him, sitting on his thighs and spanking his bare behind.

Step Seven: If you are sitting on top of a boy who is wearing no pants and slapping his bare ass, and you still need instructions on how to get laid, clip off your balls, place them in a martini glass above your television, and spend the rest of your days watching re-runs of The Golden Girls on Lifetime.

Sex with Kenny happened. It was good. His ass was great, and I took lots of pictures of it. When we were done, we lay there, and he took the camera and started scrolling through the digital pictures. “That one’s good. That one’s good. Ew, no! Bad, That one’s OK, that one’s good...”

“I’ll email them all to you,” I said, reaching for the camera, “you can choose the best ones and put them on your profile.”

“Wait wait,” he said, still pushing buttons on the camera. Suddenly, the camera made a sound I’d never heard before, three loud tones in quick succession: BEEP! BEEP! BEEP!

“What did you do??” I cried.

“I erased them,” he replied, with the hint of a satisfied smile. “All.”

I was dumbfounded. “You whaa... I didn’t even know my camera could do that!” It was true – I would never think to erase the memory card before downloading the pictures, so I’d never even checked to see if it was possible. Apparently, it was. “Why?????”

“I don’t like the idea of you having naked pictures of me. Sorry.”

Step Eight: Always expect the unexpected. Right up until the bitter end, no matter how well things are going, always be ready to be caught off guard.

Kenny had beaten me at my own game. The pictures were gone, his pants were back on. Ok, so it wasn’t a total loss – I did have an afternoon of fun drunk sex with a hot twinky boy. But I still somehow felt like I’d been beaten, and I *really* hate to lose. I guess no matter how good you think you are, or how many times you do this, there’s always something to be learned.