The first time is always the toughest. It’s my birthday, and I’m alone, so, after scrolling through the smorgasbord of beauties, I finally find the one the moves my loins in anticipation. A perfect eight with gorgeous tits and a pretty face—she was no Carmen Electra but certainly better than anything I’ve ever had. Her website pic seems to be smiling at me, inviting me. All I have to do is dial the number, and I can be smashing headboards with this hottie. Let’s see…3-1-0-5-5-5…shit! I hang up. Why am I so damn nervous? She’s just a woman—a very beautiful, never-in-my-wildest-dreams type of woman...that I can be unpeeling RIGHT NOW, if I can muster up the balls.
“Pull yourself together and dial the number,” my penis seems to be telling me. Maybe I should jack off first, so I don’t sound so desperate when I call her. Of course then, I might have some erection issues if I’m too nervous and I’ve already shot my load. God, I’m horny! Fuck it! I pick up the phone and dial the entire number. I can feel—no, hear-- my heart beating in my chest as the phone rings once…twice…three times. Oh, good…she’s not there so I can just leave a well thought out callback message...
“Hello.” A soft voice answers just before I start to hang up. Shit!
“Uh…hello. Is Jenna in?” I manage to eek out, trying not to sound nervous.
“This is she,” she says. “Are you lonely tonight?”
Silence. A lump grows in my throat. A boner grows in my jeans.
“Yes…your website says …um…that you…” Boy, do I feel like a dork.
She laughs. “Is this your first time, honey?”
“That obvious, huh?” I reply, feeling somewhat relaxed by her soft laugh and the honey word. “I have $300…and I was hoping to…”
“Shhh, sweetie” she nearly whispers. “We’ll discuss that when I see you. If you saw my website, then we’re tracking. Just tell me the time and place.”
We work out the details and hang up. I’ve got two hours to get things perfect. Two hours to ecstasy. Let the countdown begin...
I jump in the shower and scrub my testicles and anus extra vigorously. In case she’s, you know, super nasty. I meticulously clean every orifice on my body, anticipating a mind-blowing tongue bath in my near future. I hopped out, nearly busting my butt on the wet floor, and run on my tiptoes to the bedroom. I spray two blasts of Axe body spray on each side of my stomach and rub it over my chest and pubic hair. I pull out a pair of black silk pajamas.
“Nope, only Hugh Hefner can pull that one off,” I say to myself, tossing them aside. I opt for a pair of Calvin Klein cargo khakis and a black Sean John T-shirt. Relaxed but stylish. Perfect. Time hack: One hour, ten minutes, and counting.
I plan out the script in my head. Should I offer her a drink first…sort of break the ice? I look in my refrigerator. All I have is a swallow of Alize left in the bottle and some milk. I down the rest of the Alize and consider a Plan B. Maybe I’ll just take control and go for a kiss right off the bat. Play the manly, confident role. Best-case scenario: she’ll melt and it’ll get hotter from there. Worst-case scenario: she’ll think I’m a weirdo and the night will end there. Decisions, decisions.
My watch says I have 45 minutes before she gets here. I sit down on the couch and turn on the radio. The sound of Norah Jones relaxes me a bit and sets the mood perfectly. I wish I ‘d thought to get candles or something. Ah well…next time.
As I lay there, anticipating my impending fantasy, I begin to massage my member through my pants, mainly to make sure he plans to act right tonight. The partial erection assures me that he’s game. I look at my watch—15 minutes. My heart starts to thump loudly again. I feel nervous, but the Alize starts to take effect, and I breathe easy. I’m ready.
KNOCK KNOCK KNOCK. The unexpected knock at the door startles me. Damn, she ten minutes early. Shit…where are my Altiods? I find them on the coffee table and pop one in my mouth. The guest knocks again. I can tell she has little hands by the sound of the knock. I walk to the door and grab the doorknob, taking a deep breath. I’m at the point of no return now. “Man up,” I told myself to kill the butterflies in my stomach. I close my eyes and quickly pray that she’s everything I expected. I turn the knob and slowly open the door.
“Hi baby…SURPRISE!” my fiancée, Tonya, squeals, standing at the door, holding a single rose and a wrapped box. FUCK.
“Hi. Honey,” I stammer, trying not to sound shocked and disappointed---and guilty. “I thought you were working late tonight.”
“Not on my man’s birthday!” she replied. “Kate said she’ll work my shift at the hospital; and so I’m all yours tonight,” she said as she walked in and closed the door.
Talk about a “wanna get away?” moment. My mind started racing. Think…fucking think. I pulled her into a tight bear hug and held her tight. In the distance, I could hear the distinct sound of high heels coming up the sidewalk. As the steps came closer to my door, I could hear my heart pounding. Should I confess or just pretend my friends set me up? The footsteps stopped and a light knock came from the door. Here it was, my first time being unfaithful---with an escort at that---and I get cold busted. And I didn’t even get a chance to partake in the forbidden opportunity.
“Who’s that, babe?” Tonya asks with a perplexed look.
What would you do?
