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. “Now you have.” He’s smiling, so I kiss him again, longer this time, but still closed mouth. His hands are doing nothing at his sides, so I put them around me and kiss him again. This time he kisses me back. I moan a little, and once again he backs off. “S-Sorry” he stammers. “It’s okay Billy, there’s nothing to be nervous about. I just got a little excited.” I go back to kissing him, and this time one of his hands is in my hair. I open my mouth slightly and give him a little tongue. My nipples are hard, and rubbing against his chest, and I can feel his erection pushing against me. This time it’s Billy who moans, so I go for it and give him the full French kiss experience. He doesn’t do much at first, but then his tongue is in my mouth and I can tell he’s really getting into it. One hand is on my butt, the other wrapped in my hair, and as I hold him tight, I rub myself against his oh so hard erection. Then he starts gasping into my mouth and thrusting his hips against me and I know he just came in his pants.

He pulls away once more. “I’m so sorry, I didn’t mean to…” “It’s okay” I shush him, “I’m glad I turn you on that much” I rub his deflated cock “Don’t worry, he’ll be hard again in a few minutes, and I have plenty of time to spend with you.” I say with a grin. “Lets go upstairs to your bedroom.” He nods and I take his hand in mine and lead him upstairs. “Sorry about the mess, I wasn’t expecting … this” says Billy, opening a door. There’s a single bed, stuff all over the floor, geeky posters on the walls and the smell of sweat and teenage boy. I breathe it in like it’s sweet nectar and give an anticipatory shiver. “That’s fine Billy, I don’t care about the room, I just want you.”

I sit him down on the bed, and start kissing him again, my tongue a welcome invader in his mouth. I pull up his t-shirt out of his trousers and then over his head, breaking our contact briefly. I start to kiss his chest and then his nipples, whilst running my hands all over his back. I then unzip his trousers and pull them and his y-fronts down. His cum covered cock is starting to harden again before my eyes, and I lick my lips. “I’ll clean myself up.” he says embarrassed. “No” I say quickly “let me” and I put my head down and lick up his sperm, running my tongue along his length. He closes his eyes and flops back on the bed. He gasps when I kiss the tip of his cock and makes little noises when I put it in my mouth. I apply a gentle suction and move up and down, enjoying the taste of his young spunk. I put his hands on my head, and let him guide me on the speed he likes. Breathing through my nose, I manage to take a lot of him in my mouth, sucking and licking as I go, replacing his cum with my saliva. His first blowjob doesn’t last long however, and I can tell he’s already ready to cum again. He tenses up and I manage to get most of him in my mouth as he erupts long streams of cum down my throat, crying out. I swallow his load, enjoying his flavour and his obvious enjoyment.

When he’s finished, I move up on the bed, licking my lips. I’m leaning over him and say “How was that for you? Did you enjoy that?” “I’ve never felt anything like it” he says “Can we do it again?”

I look down at his deflated member. “I think you might need a little recovery time,” I say with a smile, “But yes, we can when you are ready and reloaded.”

I get up and tell him to wait there. I find a bathroom and rinse my mouth clean of the few dribbles of his cum I hadn’t swallowed. He might have been alright with the taste of it in my mouth, but I didn‘t want to take the chance. When I got back I found him sitting up, so I stepped over his comics, got on his bed and straddled him. “Hi babe” I whispered and kissed him hard, our tongues and saliva mixing together. My hands were in his hair, and my nipples were hard, rubbing against his chest. Breaking the kiss, I took off my t-shirt, leaving my breasts straining against my bra. Billy stared at them. “Take off my bra Billy. Please” I said, as he looked up at my face, going red. “O-Ok” he stuttered. He fumbled a bit, not sure where to put his hands. I told him the catch was in the back and directed him there. After a minute of pulling and pushing it, he got the hang of it and removed my bra with a proud look and let it drop to the floor.

“Do you like them Billy?” He nodded. “They’re all yours”. I put his hands on my breasts and moved them around. Oh, that was nice. “Can I kiss them?” he asks me shyly. “Please Billy, I want you to kiss my breasts, suck my nipples.” His head swoops down and gently kisses their upslopes, then he puts a hard nipple in his mouth and sucks. I put my head back and moan. “Fuck, that’s good”. He’s a bit rough at first, but I tell him what to do and it gets better. “Oh Billy, you’re making me so wet” I kiss him again and lead his hand down, inside my panties. His fingers squelch as they touch my soaking pussy. “See baby? You’re making me so horny. So wet.” I take his damp hand to my mouth and suck my own juices off of his fingers, looking him straight in the eye. He gives a little gasp and I moan in pleasure. “I want you so bad Billy, I want your cock deep in my pussy, filling me up.” I say seductively. I lean close and whisper in his ear “I want you to make me scream your name.”

I stand up and quickly pull the rest of my clothes off. I then pull his trousers and pants all the way off until he’s clad only in socks. I look down at his penis and see it is starting to rise again. That‘s another thing to love about these young virgins, they recover quickly. I give it a couple of strokes to hurry it up. “Lie back” I say “I’ll take care of everything.” I straddle Billy as he lies back on his bed. “Do you want to fuck me Billy? Do you want me to take your virginity? Do you want to put your young cock inside my tight little pussy?” “Yes, oh yes I do!” he replies. I look down, and see he’s still a bit soft, but it looks hard enough, and I can’t wait anymore. I line him up, and rub his cock against my damp slit.

His breathing quickens and I look him in the eye as he slips inside. I sit down and he pops in, going all the way. He’s not massive, but he fills me up nicely and I hiss a “Yessss” as my walls clench around his member. Oh, he feels so good. Billy’s eyes are looking at where our bodies join and he has this look of wonderment and surprise on his face. I raise my hips slowly, letting us both feel it all, the movement of his wonderful cock inside me, then plunge down again. I start off slow for a few minutes, enjoying the rhythm, and soon he’s moving his hips with mine, his hands clasping the sheets tightly. He moans and gasps as the bed starts to squeak. “Yes, oh yes!” I exclaim. “More Billy, I need more. Please fuck me harder Billy.” I can feel the tension rising inside of me as he starts to pound away. “ Oh yes! Yes! Fuck me Billy, fill me with your spunk! I need you so bad, please Billy! Oh yes!” The bed’s banging against the wall now, but I barely notice as I start to cum, and cum hard. “YES! YES! YES! OH….FUUUCCKKKK..…”

By the end of it I’m screaming gibberish, every movement of Billy’s cock is giving me aftershocks of pleasure as I collapse on him. I lay there, getting my breath back, but after a while I notice him fidgeting. “What’s wrong babe? Didn’t you like that?” I ask him. “N-No, it was the best moment of my life, it’s just… um… I didn’t, y’know”. I feel him still hard inside my pussy, while my juices leak onto his body and his bed. “Oh sorry babe, you didn’t cum yet?” I carefully turned us over without pulling him out. I would have just rolled us over, but the bed was too small for that.

I pull him down for a sloppy kiss, then stare him in the eye. “Fuck the hell out of me.” I instruct him and wrap my legs around his body. He’s eager to start, so eager he falls out and more of my pussy juice leaks onto the bed, but then he’s back in, I’m getting tingles and his tongue is in my mouth and it’s good, it’s really good. Every time he thrusts into me, there’s a squelch and the beds banging against the wall again. He starts to kiss my neck, so I push up one of my breasts for him and he starts sucking it again. The pleasures overwhelming and it’s not long before I’m screaming his name, then with a loud exclamation he cums. His face contorts and I feel his seed coat my inner walls and then I’m cumming again too and waves of pleasure hit me. When I recover, Billy’s draped on top of me. I kiss the top of his head. “I think the neighbours may of heard us.” “I think the whole road heard us.” he retorts. “Now they’ll know what a stud you are.” I say with a grin. I roll us onto our sides and hold him close as he starts to doze. “All the girls will want to fuck you, you’ll get all the pussy you can handle.” I whisper as he falls asleep. I’m pretty exhausted too and catch a quick nap.

Next thing I know it’s 10pm, and we’ve got an hour before his parents are back. Billy’s erect again and I can feel him rubbing against me in his sleep. Seems like someone wants more. I wake him with a kiss, my tongue darting into his mouth and caressing his. He moans and kisses me back, then his eyes open. “Hi” he says. “Sweet dreams?” I ask. “Better in real life” he replies.

I give him another quick kiss then take his hand and get us both out of bed. “Come on” I say, “I want to make some more memories for you.” I lead him out of the room, both of us almost completely naked, and take Billy downstairs, into the sitting room. I kiss him again deeply, gently stroking his cock, then pull away and bend over the arm of the sofa. I look back and say “I want you to fuck me doggy style Billy.” “Ok” and with that he takes himself in hand and pushes his penis against my pussy. With a slight movement he slides in, filling me up until I feel stuffed full. He holds there a moment, bracing himself, then he’s swiftly pulling out and then he’s filling me again and it feels good. Like really good. With every stroke, I spread my legs further, and he speeds up. I’m moaning and gasping, he’s making this cute little panting noise. I imagine he’s probably not used to getting this much exercise, but he’s certainly giving it his all and it’s definitely worth it. This kid is going to be a fucking machine with a bit more practice. Each thrust into me lifts me up in the air a bit, it feels like he trying to push right through me. I’m almost there when he stops. Out of breath and sweating, he apologises. “I’m sorry, I can’t keep going. You’re exhausting me.”

“That’s alright babe.” I then take his hand again and lead him into the kitchen. I sit him down on one of the kitchen chairs and straddle him. “I’ll finish you off.” I lower myself down and let his juice covered cock fill me again and soon we’re at it again. Thankfully it doesn’t take too long as I think we almost broke the chair. “I’m cumming Debra! I’m cumming!” he shouts and it feels like it’s going to shoot straight through me and he’s hitting just the right angle and I cum again, howling like a banshee.

I drape myself over his naked body, our juices running onto the wooden chair as he pulls out. “Thank you darling” I pant “You were good, very good.” I pull him up off the poor abused chair. “But now we’ve got to clean this up before your parents are back. They may know you had sex, but I’m sure they don’t want to see all the evidence everywhere.” He blushes a bit. We go to work, with cloth, washing machine and air freshener and it doesn’t take long to do. I look over at Billy, who sagging a bit now and think that he’s certainly going to have a good nights sleep tonight. By the time we’re both dressed it’s just gone 11pm.

“Thank you Debra, you were great. I never expected this. I’ll never forget tonight.” “I bet you’ll never look at the sofa they same way again.” I say with a smile. He smiles back, “Can I see you again? I have money of my own.” “Sorry Billy, this was a one time deal, but trust me, you can get any girl or woman you want. Tell your friends about what happened, just leave out the part where I got paid. Just tell them you got laid with an older woman, and that you shagged the hell out her. I don’t think I’ll walk straight for a week.” And with that I gave him a kiss goodbye and left. As I started to cross the road to my car, his parents pulled up. I waited as they came over to me. “How did it go?” said his dad. “Really great. He definitely had a good birthday. I don’t think you need to worry about his confidence with women anymore.” I said my goodbyes, flopped into my car and went home for a well deserved rest and to dream of virgins.

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