Cherry Popper

Hi, my name is Debra and this is a snippet of my life. My main job is a very boring, pays the bills, call centre gig. Making everybody’s life a bit more miserable. My part-time job/hobby is the interesting one though, I try to balance the dark side of the call centre, with bringing a bit of joy into peoples lives. Well, young men’s lives. I’m a Cherry Popper you see. I’m not a hooker, I want to make that quite clear. Yes, I take money for it, and yes, I fuck strangers, but it’s more than that.

You see, I have a kink for being their first, it really turns me on, and they definitely enjoy it, so it’s more a mutual satisfaction arrangement. The money is just a nice gift, and helps me look a little less strange. I find people prefer to think your doing it just for the money, rather than you just enjoy taking their ‘innocence’.

I don’t advertise of course, but word gets around, and so does my number, and rarely a month goes by without me taking a virgin’s cherry. Male virgin of course. I’ve had a couple of lesbian experiences in my life, when I was lonely or curious, but generally I need a hard cock in my pussy.

The ones that need to pay for it, well lets just say there’s usually a reason for it. You don’t usually get a young Brad Pitt. Fat, thin, spotty, ugly, it doesn’t matter to me, I enjoy their enthusiasm, their inexperience, the look on their face the first time they cum inside a woman, rather than their hand. This is the story of one of my clients.

It was his dad who called me. He had been given my number by a friend of his, who had gotten it of someone else, in a chain of suburban tattletale. He told me his son was very shy, had no confidence with women, and he thought I could give him that. I met him at his house one afternoon when the kid was out to finalise the details. Doug was there with his wife Anna, a typical middle class family in a typical middle class house. Their son Billy had his birthday coming up on Friday. I was to turn up at 7pm, they would have gone out and I was to seduce their son and fuck some confidence into him. That would be no problem, it was making me horny just thinking about it. They paid me the money and showed me a photo of Billy. He was quite sweet, nerdy looking, but in a cute way. I was looking forward to Friday!

So Friday afternoon comes around, and I make sure I look good. I’m all shaved and showered, with a subtle application of make-up. I’m wearing a small dress, and a tight t-shirt with delicate underwear and a nice bra that pushes up the girls. At 31 my breasts haven’t started to sag too much yet, but it’s always good to give them a boost. I look good, even if I do say so myself.

So I drive over to Billy’s house, parking across the street. At 6.50 his parents leave in their car, his mum giving me a smile and a thumbs up as they pass. Checking myself in the car mirror one last time, I then saunter over to the front door and ring the doorbell. Billy opens the door and says “H-Hello?” He’s dressed in a t-shirt and black trousers, chubby, but not fat, hair a little greasy and untidy, but I still want to run my hands through it.

“Hi, you must be Billy” I say with a smile. “I‘m Debra. Happy birthday!” “Um, thanks” He says, looking down at the floor. “If you’re looking for my parents, they just left.” My smile widens “No, it’s you I want Billy. Your mum and dad paid me to be your birthday present.”

“What?” he says, looking up with a confused and slightly hopeful expression. “What do you mean?” I close the gap between us, put my hands on his shoulders and pull him down until I can whisper in his ear. “I’m your birthday present. First you unwrap me, then you get to fuck me…” I then lick his ear. He backs off quickly. “You’re joking, right?”

“No joke, Billy. Don’t you want me?” I say as I put on a sexy pose. “I, I, uh, well” he stammers and swallows as I wait patiently. “Yes” he says in a quiet voice, and then once more, this time with more determination.

I smile again. “Are you a virgin Billy? Be honest.” He looks down at the ground again and nods his head. “Have you even kissed a girl yet?” He squeaks out a no. “Good!” I say, and he looks up at this. I walk further into the hallway, until my body is pressed up against his and kiss him gently on the lips.