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Carrie's Cherry Gets Popped

Stepsister gets her cherry taken...

Let me introduce myself; my name is Jackson. Blame my mum for that. She had a one night stand with a guy named Jack when she was 17 and thought it’d be funny to call me Jack’s son when I came along nine months later. She loves me, for sure, but the woman’s a flake. Always has been. She also jokes that I’m pretty normal, considering the amount of drugs she did during her first trimester. Didn’t notice she was pregnant.

Dozy cow.

Anyhow, she has managed to sort her life out. Married a bank manager called Kevin, who is as boring as he sounds.

Boring is good for my mum: uneventful keeps her away from the drugs.


Anyhow. When my mum got married to the bank manager, I inherited a stepsister, Carrie, or as I liked to call her ‘that bitch’. As in that bitch ate my pizza (didn’t have your name on it); that bitch stole money from my wallet (It was raining. I needed money for a taxi); that bitch told my girlfriend that I’d had another woman in my room (my mate’s girlfriend with my mate. We were playing Xbox and eating pizza). This last one had caused trouble; my girlfriend had decided to withhold sexual favours until ‘she was sure’, whatever the fuck that meant.

So I was back to bashing the bishop to various vids on PornHub, trapped between losing the hottest girl I could hope to maintain in college, or heading out to new uncertain pastures.

“S’up?” Carrie asked, making me jump as I raided the fridge before embarking on another masturbation marathon.

“Like you care,” I said, not even looking at my irritating sixteen-year-old stepsister.

“Aren’t you going to ask me why I’m not in school?” Carrie asked, as I poured a drink from the fridge’s water jug.

That did make me think. I looked at her for a second, eyeing her slouchy demeanour and stupid pyjamas. Why wasn’t she in school? It didn’t interfere with my plans for the day, so I wasn’t interested. “No.” So long as my stepsister stayed on the other side of my bedroom door, the fact that she was in the house made no difference to my plans for the day: wank, shower, football, food, beer and bed.

“I’m…” Carrie said.

“Boring?” I suggested. “I’m going to my room.” Balancing a bag of crisps on the plate, I pushed the fridge door shut with my hip and squeezed past my stepsister, determined to get fed and watered before jerking-off to random porn clips.

I got upstairs, closed my door to the world, and then put on some music before slipping my gaming headset on. I browsed through the latest uploads, not paying much attention to genres, concentrating instead on the enjoyment of the women involved and their resemblance to my own absent girlfriend.

The gaming headset meant I didn’t hear Carrie sneaking into my room. There was no lock, but she knew not to come in when the door was closed.

It was sixth sense that told me I was no longer alone.

“Didn’t your mum teach you how to knock?” I asked, scrambling my cock back into my pants as I pressed Windows+D. I was pretty sure that the flared headrest meant she hadn’t seen much, if anything from the open doorway.

“I did knock,” Carrie said smartly. “You just didn’t hear. Your mum’s on the phone.”

“Tell her I’ll call back.”

“She said it’s important.”

“Fuck’s sake,” I muttered, making sure I was decent as I rolled out of my chair.

It wasn’t important. It was pointless bullshit, as always. Shopping - as if I care!

The same reason I felt sure that Carrie hadn’t seen what I was doing when she’d been standing in my room’s doorway meant I didn’t know she was there until after I’d closed my bedroom door. My chair span slowly round into the room to greet me, and nestled deep in that faux-leather sanctuary was my stepsister. “Jackson, Jackson…” she said, wagging a disapproving finger. “What would your girlfriend say if she knew about this?” I could see that the minimised windows had been reopened and arranged on my computer’s desktop.

“Listen freak show,” I said, grabbing hold of the top of the chair. I was properly angry and Carrie shrieked with fear as I loomed over her. I saw her eyes go wide and I followed her gaze down as she grabbed her crotch.

There was a growing puddle of pee as Carrie pissed herself in my seat. “Oh shit,” she cried, clutching at herself as she ducked out under my arms and went to run from the room.

“Carrie!” I called after her, feeling remorse replace anger. I’d closed the bedroom door behind me and I caught my stepsister by the arm before she could escape. “Carrie…”

“Please, don’t hit me.”

Hit you?” I was shocked, and my stepsister could see it. “I’d never… why would I hit you?”

“Because I’m such a little shit?” she suggested, using one of my names for her. She was crying now. Sobbing. Big snotty sobs. “Because… because I stole from you. Because I tried to break up you and your girlfriend.”

“But…” I decided to ask a different question. A direct one. “Carrie?” I waited until she looked at me. “Carrie, has anyone ever hit you?” The evasive eyes told me what I needed to know. “Who?”

What happened next was not my proudest moment. Carrie cuddled in against me and I became aware of her very petite figure in soft pyjamas pressed against my athletic body, with only boxer shorts for protection. My cock inflated and there was nowhere it could go, except dig into her belly.

Of all the inappropriate boners to have happened throughout history, this one was one of the worst.

And yet, Carrie seemed to squash in closer, rather than pull away.

“Carrie,” I said, decided that I should at least acknowledge what was happening. “I’m sorry about my…”

“Hard-on?” she suggested.

“I was going to say behaviour. But… well, yes. That as well.”

“As swell, you mean.” She laughed snottily, as her fingers explored my bare back, making the erection worse. “It’s OK.” It being okay, I pulled my stepsister in closer and ran my fingers over the tangle of greasy blonde locks as more sobs came. “It’s OK.”

“I… I feel safe when you’re holding me like this.” I wanted to ask when Carrie didn’t feel safe, but the tears were drying and there would be another time for that conversation. “I’m sorry I peed in your chair.”

“I’m sorry I scared you,” I reciprocated.

There was a kind of pregnant pause, with both of us wondering how the hell we were going to deal with what felt like a seismic shift in our hateful relationship. I made to pull away… and then we were kissing. A great washing machine on its fast-spin cycle of tongues and lower down, Carrie’s hand began inexpertly rubbing the crotch area of my boxers, mostly avoiding the pleasurable parts of my cock, instead applying uncomfortable pressure to my ball sack.

In the end, I had to move her hand to save her doing me an injury. “Carrie? Have you ever…”

“No,” she said, quickly. I looked into Carrie’s eyes and we shared a moment. Something spiritual. Like our souls had found each other in the dark void of space and were now dancing, vowing never to let each other go. “Never.”


The word popped into my head and gave my cock an involuntary boost of blood.

“Shit! That feels really, really hard now.” Carrie laughed. “Now I get why they call it a boner.”

“Uh huh.” I couldn’t get words out as my cock took over my mental faculties. My cock wanted to have sex with my sixteen-year-old stepsister.

Right now.

I didn’t; my brain was screaming at me, telling me that it was a terrible idea… a fucking terrible idea. But my cock was pointing out the advantages of the living, breathing woman in my arms over one made of a million pixels on my screen.

“Uh huh?” Carrie asked, mocking me. “That’s the best you’ve got? Well, I guess I’m just going to go ahead and see what your cock looks like.”

I desperately wanted her to do it; I equally desperately wanted to stop her, but in the end I reasoned that it was her decision. I wasn’t making her do anything.

Just as I finished my reasoning, Carrie pulled my boxer shorts down, revealing my seven-inch cock.

“Holy shit! That thing is a monster. Jackson, I never thought you had one that big.”

“You’ve thought about how big my cock might be?” I asked, my voice a worried grumble.

She did something complicated with her eyebrows which may have passed a lot of information to someone who could read eyebrows. “Like yeah! You’ve got no idea, how often I’ve thought about that.”

“How often?” Carrie took a grip and began to jerk my cock.

“Erm, most nights.”

“You’ve been masturbating about doing this?” Carrie nodded.

“Not just this. I imagined what it would feel like inside me. Ever since we started living together.” Carrie took a deep breath. “There’s been a couple of other guys who I could have… but I’ve been saving myself for you.”

“Wait. Hold on. You’re saying that you’ve been saving your virginity for me?”

“If you want it.”

“Yeah, I want it,” I admitted to both of us. “Today. Now.” I saw something flash across Carrie’s eyes.



Maybe excitement.

“Is that OK?”

“I want you to be my first.” Which to me, sounded like my stepsister wasn’t ready.

“Are you on?” I asked, trying to be sensitive.

“My period? No.” But there was something. We stood there for a few minutes, while Carrie continued to jerk my cock and play with my balls. There was no way I could guess what it was and I was going to come if I didn’t move the action forward soon.

So I started.

I put my hands on Carrie’s hips, making her gasp. As she lifted her head, I laid a deep passionate kiss on her lips and eased my thumbs down the front of her pelvis, tracing down inside her pyjamas and knickers towards her piss-soaked pussy.

Oh yes. That was probably why my stepsister was a little nervous. The girl had peed herself because I’d scared her.

My fingers at the back eased the wet material of both garments free from Carrie’s buttocks. They stuck at the top of her thighs, but her private parts were now fully exposed. “Let me see,” I said, escaping the kiss by taking a half-step back.

A grin ripped at my face as I saw how pretty she was down there… and as I traced her slit with my fingers, how wet… and clearly not just from pee. Carrie’s soft flesh slithered around my fingers as I pushed them deep between her legs.

Carrie whimpered. “I can’t believe you’re touching me after I…”

“How does it feel?” I could tell by the stationary hand gripping my cock that it felt all kinds of wonderful.

“I’m imagining your cock inside me. Right now,” Carrie confessed. “It feels more real…” All the breath in Carrie’s lungs was released as I circled the entrance to her vagina and pushed gently up and in.

My finger penetrated to the first joint.

I let it sit there for a moment. “Has anyone ever fingered you before, Carrie?” I could tell by the way she was biting her bottom lip that this was a first.

My stepsister shook her head.

“So, I’m the first?” Carrie nodded. Leaning forward, I eased my tongue into her mouth and kissed her softly. With our foreheads pressed together, I whispered a truth. “I am one lucky bastard.”

Carrie snorted with desire and laughter.

“I’m all yours,” she murmured. Carrie pulled back a little and let go of my cock, although I kept my finger inside her virgin vagina. She pulled off her pyjama top, revealing a pair of beautiful tits which bounced and heaved in a way which was defined by youthful solidity. “OK, where was I?” she whispered. I groaned with contentment as she slipped her hand back around my cock and started pulling up and down. “Good?”

“Like you wouldn’t believe,” I admitted to both my stepsister and myself. That remark earned me a sexy glare.

“I bet I can make it feel even better,” she said in a whispered breath. I knew what was coming as soon as Carrie lowered her head. The warmth of her breath both tickled and soothed my cock… and then I felt her soft mouth and the wetness of her saliva.

“Oh fuck!” My cock had been right about swapping PornHub for a real-life blowjob; it felt fucking amazing. Carrie came up for air, leaving my cock jerking hopefully.

“Am I doing it right?”

I laughed. “You’re doing it perfectly.” I made a mental correction as Carrie went down on me again – what she was doing now was perfect; faster, deeper and more confident.

And then she stopped dead, giving me the frustrated ache of orgasm denial. “I want to try it.” I knew what she wanted to try but wanted to hear her say it.

“What do you want to try?”

“Proper sex.” I couldn’t help but smile and time and bodies seemed to blur as we melded together, ending up on the bed with me over Carrie, between her spread legs.

“You sure you want to do this with me?” I asked, touching my cock into the bottom of that slippery slit.

“Technically,” Carrie said, smiling so brightly that she might have been auditioning for a toothpaste commercial. “I think it’s already too late to ask that question.” My weight was on Carrie’s thighs; as she spread her legs, she controlled the penetration, allowing me in deeper and deeper.

With her physical permission, I slid my snake in and held it there, surprised that it had been so easy.

“You OK?”

“Oh yes. That feels… nice, Jackson.” Carrie’s whispered voice sounded far off.

I partially withdrew, before easing back in, always mindful that this was a virgin and a girl that would be around in my life forever. “Don’t screw this up,” I thought to myself, pushing back in hard enough to make her sigh and moan. Carrie shifted underneath me, spreading her legs wider and pulling her knees back -  in short fully opening herself up to me.

Either she’d been watching some videos or her body was acting on instinct.

“Oh Jackson… that feels so…”

The fragrant scent of sweet, virgin pussy juice filled my nostrils and I started to thrust instinctively.


Something popped against the top of my cock. I stopped immediately. “Oh shit! That fucking hurt.” I withdrew and there was blood on my cock.

“I’m… sorry,” I said, unsure what I had just done to my stepsister’s pussy.

“What for? You just popped my cherry. Just a second.” Carrie reached for the box of tissues I used to collect my spunk when wanking, and wiped between her legs. “I think I’m good to go… so long as you’re not squeamish.”

It was hard to be squeamish with a pretty naked woman lying on my bed with her legs spread, inviting me to fuck her.

“I’ll be gentle,” I promised.

“Not too gentle, I hope.”

I resumed the position and this time my cock sank in deeply in one thrust. It was incredibly tight in there, with a cylinder of muscle just inside the entrance acting like a tourniquet, but she was able to take me balls deep.

It wasn’t frantic fucking and that made the experience all the more intimate for us both; it was almost tantric the way the pleasure built with incremental steps and it was after a full half hour that I finally reached the plateau of my orgasm. “I’m going to come, Carrie.”

“Oh thank God! I’ve been edging for twenty minutes. Just tell me when.”

‘When’ was about 30 seconds later, since there was no resisting as I watched Carrie pulling and twisting a nipple while rubbing her clitoris. My cock and balls erupted into fiery ecstasy and Carrie joined me in a roaring, cleansing sexual release which seemed to go on and on and on.

My heart was still racing as we finally lay side-by-side on the bed, not really knowing what to do.

Eventually, Carrie said calmly, “It’s going to be really hard to hate you as much now.”

I laughed with relief. “The feeling’s mutual.”

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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