The Lollipop Kid

"We need to stop at the Sugar Shop," I tell Greg. Meeting in Vegas for the weekend we're ready for a night of dancing and debauchery when he reveals that he's been having a hard time nailing his hotel roommate. The two have a hush-hush hookup history, but that was long ago. Their once sordid love affair has all but turned into a casual friendship with occasional flirting. "Then why are you two sharing a bed?"
"Because I'm testing the waters," Greg says, sauntering along the strip in cowboy boots. "I decided Vegas would be the perfect place to put myself out there, but he needs to make the first move so I can blame him when it all goes to shit." We take the thousandth flight of stairs into the thousandth mall for the day but he doesn't complain. He likes the way it tightens his butt. "I want the cock...his cock! Do I have to spell it out for him?"
"Some men need a prompt," I advise, heading into the Sugar Shop, where I purchase a red lollipop in the shape of a gaming die. "Try this," I say, handing it to him. "It's a no-brainer. He'll be tired from gambling when he comes home. He'll be drunk, horny...unguarded. And you'll be on the bed casually licking an innocent lollipop. Taking it in ever so gently."
He eyes me dully. "A little obvious, isn't it?"
I push him to the outside, where colors and light sparkle in a fountain, reflecting on a billboard for the Bellagio Hotel. "Get over it. Sometimes obvious is all a gay boy has," I tell him. "Besides, it can be a great tool, especially when defenses are down. Now, let's talk about positioning."
"Positioning? This is too complicated," he protests, as a woman in a dirt-stained Hello Kitty costume panhandles nearby, causing him to contemplate. "Do you think Hello Kitty has these problems?"
"Hello Kitty has a lot of problems, beginning with hygiene. My God. I can't believe people let their kids near that thing. The prostitutes in this city are cleaner." I steer him to the other side of the sidewalk, beyond the men dressed like Superman and Iron Man. "Now, again, think positioning. You need to be ass up on the bed when he comes home. And make sure you're wearing slinky undies."
"Ok. Ass up. Slinky undies. Lollipop," he agrees. "Got it."
He's primed, ready, and lubed for action 'til the next morning when I get a frantic phone call. Things didn't go according to plan. He awoke with the ability to sit without pain. He didn't get butt-punched and he isn't happy. He meets me at the casino. "I did everything you told me," he says.
"Lollipop?"
"Yes."
"Sucking gently?"
"Yes."
"What about the slinky undies?"
"Boxer briefs."
"Boxer briefs!!!???"
"Nothing else was clean."
"Well no wonder he wouldn't fuck you. Nothing says 'I'm going to bed' like boxer briefs. You might as well have shit on the floor."
Upset, he puts a quarter into a slot machine and pulls the handle. "So much for waking up in Vegas. That Katy Perry song made it sound so fun."
Things only get worse later that night when Greg's man begins flirting at the casino with some random guy. The incident leads to an argument, which Greg calls a heart-to-heart conversation. It's more entertaining than the Celine Dion show 'til the two begin rehashing all that went wrong the first time they fucked. Then it plays out like the Titanic. We're all sinking. And I'm the bastard for taking the only life preserver, returning to my room.
"I can't believe you left me," Greg says, sunbathing at the pool the next day. "It's your fault this started. We were up all night-" He rolls his eyes. "Talking."
I sigh. "I don't get it. You must be the only person alive who can't get laid in Vegas."
"I know. It's pathetic," he admits, sipping a red cocktail. "But I tried everything."
I roll over to allow the sun on my back, thinking how many times have I heard this, from how many friends? He never calls me. He doesn't seem interested. He doesn't give me enough attention. Why won't he fuck me? At some point in every friendship there comes a time when someone starts drowning. It takes tough love to air the truth.
"Well, you know what they say in Vegas. When you're down on your luck...." I give him a wink, tossing him a pocket vibrator. "Try another machine."