Sherry's Cherry

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I withdrew my cock nice and slow, trying not to groan so she wouldn't know how much I liked it, stopping when my cock was halfway out. I looked down to see my shaft coated in my daughter's virgin blood.

"Is that better?"

She sniffled, shaking her head. "I think we should take it out all the way. It's too big for my pussy. I don't like how it feels."

"Aw, honey, I'm sorry," I said, reaching for her cheek, subtly thrusting my cock back into her tight little cunt.

"Ow, Daddy! You're pushing it back in again!"

"Oops," I said. "Sorry, baby."

I slowly withdrew again, marveling at how tight she was. I'd never been with a virgin before. Even my cheating whore of an ex-wife was loose before I fucked her after senior prom. I had to marry the bitch nine months later. And before her, I'd only had a few blown out cheerleaders. But my little girl, Sherry, fucking hell, she was the best I'd ever had, and I hadn't even fucked her yet, technically.

"Daddy, you have to take it out. We're not supposed to leave it in this long, are we? I mean, it'll be like sex if you cum. You said so."

"I'm not going to cum, baby."

But I was going to cum. Her cunt was a vice.

"Please, Daddy, take it out," Sherry said, her lips pouty, like she was asking me for a new car on her birthday.

I sighed. "Okay, baby."

I slowly withdrew my cock from her pussy. When it popped out, her cunt made a soft suction sound. I stared down at my hard dick, throbbing in request to get back into that hot, hot hole. Sherry, however, sat up slowly, scooting back on the desk, putting her feet back up and spreading her legs so she could look down at her red pussy.

"There's so much blood."

"Well, we did break your cherry. Some of it may have been left over from your period."

"Am I going to be okay?" she asked.

"Let me see," I said.

Sherry kept her legs open as I knelt down and examined her pussy, spreading her lips apart with my fingers. It was a mess, but I could see the remains of her hymen. Fuck, I just wanted back in there so bad, I didn't care what I had to do... or say.

"Honey, I think your hymen isn't fully ruptured yet."

"Huh?" she said, looking down at me between her legs. "How's that possible?"

"I didn't thrust hard enough the first time. Baby, I'm going to have to go back in there."

"But, but it hurt so much."

"I'll try to be a little gentler this time, but we can't leave it like this."

"Daddy, I don't know..."

"Baby, if we don't I may have to rush you to the emergency room. You have to trust me. Be a good girl and lie back."

"Oh, god..."

Sherry did as she was told, lying back on the desk, once again scooting her butt all the way to the edge, her toes gripping the wood as her legs spread wide. I stepped between them again, my cock throbbing in thanks. I put the mushroom head against her slick hole, prodding it, listening to my daughter's little whimpers. Then I pushed in and she lost her breath, pinching her eyes shut.

"Ow, ow, god, Daddy, it's so big."

"It's okay, baby girl. Daddy's got you," I whispered, but I was pushing in deeper and deeper until I hit the back of her cunt. I groaned in relief to be back in this exquisitely tight hole. Sherry looked down again, her eyes locking on the base of my cock sticking out of her pussy.

"It's all the way in my tummy again, Daddy," she said, breathing through the pain. "It hurts."

I put my hand on her stomach, rubbing in circles around her belly button. "You're going to be okay, baby. Listen, Daddy has to move his cock around a little, make sure your hymen is completely broken."

"Like thrusting? You can't thrust. It will make you cum and that's like sex."

"It's not thrusting; it's more like... rocking. Just stay still."

I held her hips and gently grinded my cock into her pussy. She was making little noises as I moved around inside her, somewhere between a whimper and a moan. I slid my hand down to her cunt and gently began rubbing her sensitive little clit. She definitely moaned that time.

"Daddy..."

"Yes, baby?"

"I don't think you should do that."

"Why not?"

"It makes me feel weird."

I smiled at her. "Weird good or weird bad?"

"I don't know, but if I like it too much, I'll have an orgasm, and then it's like sex. You said so."

"I just don't want it to hurt you anymore," I said as I pushed into her deeper.

"Ow, god, Daddy. It's in so deep. Can you take out a little? Please, just halfway."

"Sure, baby."

I withdrew my cock partway, resisting the overwhelming urge to ram it right back into her cunt.

"Better?"

"Yes," she whispered. "Your penis is so big. I don't know how it didn't break my cherry the first time. Is it time to take it all the way out yet?"

"Honey, to be safe, I should really thrust into you a few more times," I said.

"Daddy, I don't---oh!" I thrust my cock into her, ramming the back of her pussy. She whimpered, holding her tummy. "Daddy, what are you doing?"

"I have to make sure your hole is clear, baby," I said, withdrawing slowly, getting ready to push back in. "Just a few more thrusts."

I shoved myself back in and she yelped. I pressed hard, feeling my cockhead bending.

"Ow, daddy, not so deep!" she said, pushing on my chest to stop me, but I already started to pull back. As soon as her hands left my chest, I rammed back in. She slid on the desk. "Daddy, stop! You're not doing it how you said you would!"

"Baby, I'm just making sure you're going to be okay," I said, but then I began pumping my cock in and out of her. I couldn't take anymore pretend-time, I just needed to fuck, and her cunt was so tight.

"Daddy, slow down!" she whined. "You're thrusting again. You said that's like sex. Daddddy!"

"Fuck," I mumbled, but I was lost to words. I had a hold of my daughter's hips and my cock was ravaging that little red pussy, all while I listened to her little whimpers. I couldn't help myself. I was going to cum.

An alarm was going off in my head, telling me to pull out, but if I couldn't hear my daughter crying for me to slow down, I couldn't hear that either. I groaned and exploded inside her. Semen came pouring out of me, emptying into her teenaged womb, but still I kept thrusting, letting that unbelievably tight pussy milk my shaft for every drop of cum in my balls.

I looked down at my cock, still stuck in Sherry's cunt. Then I looked up at her. Her lower lip was trembling between her teeth. I wasn't quite sure what to say to her, to be honest. But I was going to have talk my way out of this somehow.

"Uh, honey, I think you're pussy is all better now."

"Are you going to take your penis out now?" she asked.

"Yeah, I think that might be safe," I said.

I stepped back, slipping my gooey cock from her cunt. A strand of cum connected us until it snapped back and dripped on the desk. Even more semen was leaking out of her pussy. Shit, how to hide this?

"Uh, don't move, Sherry. Let me get something to clean up the blood."

I quickly moved around behind the desk and took out a roll of paper towels. I ripped off a few sheets, giving my cock a quick wipe. It came away with more blood than cum.

"I'm just going to clean you up, okay, and check on your pussy."

"Okay, Daddy."

She remained still on the desk as I knelt down, wiping her cunt with the paper towel. Sperm was still leaking out of her. Shit.

"Well, honey," I said, standing up, my cock hanging down obscenely, "I think the procedure was a complete success."

"Really?" she asked. She reached down, touching her pussy, slipping her finger along the slit, momentarily pushing it inside. She pulled it out quickly. "It feels really gooey down there."

"That's just the blood... and your vaginal fluid."

She looked at her fingers, and I gave her a paper towel to clean them off. "So I'm going to be okay?"

"Yup, you sure are. Why don't you take a shower, clean up, and head off to bed? If you have any other pain, just let me know and I'll examine your pussy again, okay?"

"Okay, Daddy," she said, hopping down from the desk, leaving a puddle behind, which I quickly wiped up before she turned back. "Daddy? We didn't really have sex, did we?"

"No, no, baby. It would have happened just like that with the dildo."

"But you kept thrusting into me, even when I told you not to because it hurt."

"I did it because I had to make sure your hymen was broken properly. I know it seemed rough, but it was for your own good. You can't ask the doctor to stop the amputation when the leg is halfway off, can you?"

"I guess not. It just hurt so much, and my pussy feels so sore."

"I know, sweetie, but it'll feel better in a couple of days, and more importantly, you're much healthier."

"And I'm still a virgin?"

"You sure are," I said. "Give your father a hug, kiddo."

She shyly hugged me, though she kept one hand covering her pussy, as if I hadn't seen it already. I held her for a moment, my cock pressing up against her stomach, and kissed her forehead.

"Sleep tight, baby."

"You too, Daddy."

The next day, I whistled my way to work. Even the same mundane questions that I got from patients didn't bother me.

"Doctor, I think I'm sick."

"Doctor, I think my temperature is high."

"Doctor, I think a hooker gave me Chlamydia."

All the same. Take two of these and don't call me in the morning. But I began plotting: how to get back into Sherry's pussy? I had to have her again, and again, and again, soon. But how? I decided to seek medical advice from a colleague over lunch.

"Bob," I said, "have you ever fucked a patient?"

Dr. Bob took his time chewing his sandwich before he answered. He had been something of a mentor of mine when we worked at the hospital together. Since then, he'd left to start his own private practice, and then he asked me to join him. He was much older than I was, and much wiser. He finally swallowed his mouthful.

"Why do you ask, Paul?"

"Well, hmm, how do I say this...?"

"Just tell me it wasn't in an exam room. You know there are strict guidelines."

"Oh, no, it was at home."

"Oh, fine then. Yes, I've fucked dozens of patients. I do have the common courtesy to do house calls though."

"Right," I said. "Anyway, this patient happened to be a virgin."

"You lucky son of a bitch."

"Yes, well, she was asking medical advice because her hymen was microperforated. She didn't want to see a gynecologist and she was terrified of surgery, so I told her the best alternative was penetration, and I fucked her."

"I once told a woman she could get colon cancer if I didn't use my penis to feel for tumors. Never seen someone happier to be fucked like a dog. Don't even get me started on mammograms. What's your question, Paul?"

"Touche," I said. "My question is this girl's pussy was incredible. I've got to have her again. But I can't exactly pop her cherry twice. What do I do?"

Dr. Bob was chewing again. "Ah, the age old question of how to fuck a woman under medical pretenses. Easy enough. Tell her penetrating the hymen is like getting her ears pierced. She has to be penetrated again or infection could set in."

"That will work?"

"If it doesn't, just bend her over and take her. Women prefer that."

"You are truly an inspiration, Bob."

"Yes, that's what my wife tells me. Lunch is on you, by the way."

I had a plan! Yes, Dr. Bob had given me the key to Sherry's chastity belt. It was a silly idea, ridiculous even, but my daughter was book-smart, not sex-smart. I would be back inside her little cunt by the end of the day. Fuck, I couldn't wait!

I made it home around 6:00 p.m. The house was quiet, the TV off, no sounds at all. Sherry had to be home though. Her car was parked in the driveway, and the poor girl never hung out with friends after school, unless you counted the local librarian as a friend, which she probably did.

I found her in her room. She was lying in bed, curled up with a book, still wearing her school uniform. I vaguely wondered why a Catholic school would design a girl's uniform with a short skirt and a skin-tight white blouse, but then, I wasn't complaining. Shame on me.

"Sherry?"

She looked up from her book, unfolding her feet from under her, straightening up. "Daddy, hi. I didn't hear you come in. I was reading."

"That's okay. How are you feeling?"

"Okay, I guess. How was your day?"

"Fine," I said. "How, uh, how's your vagina feeling?"

"I'm, um, still pretty sore."

"Sure. Anything you want to talk about or...?"

"No, not really. I kinda just want to put it behind us, you know? It's sort of awkward to talk about."

"Sure, I understand," I said.

"I kind of feel like, I don't know, more experienced than I was before, like I know about sex now, more than I wanted to know."

"Well, it wasn't really sex," I reminded her. It sounded stupider and stupider every time I said it. "What I mean is, what we did was no different than a medical procedure. I don't want you to feel uncomfortable because I was the one who performed it."

"Yeah, I guess not. I mean, it is totally weird to see your father's penis in the first place... and then have him stick it in your vagina, but, you know, I guess every girl has crazy stories like that, right?"

"Uh, sure."

"We'll probably look back and laugh," she added.

"Of course we will."

She smiled. "Well, um, I'm going to finish my book. Call me for dinner?"

"Actually, honey," I said, coming into the room and sitting on the edge of her bed, "before we do dinner, I'd like to examine your vagina again."

Sherry immediately looked nervous. "Why? It's okay. I looked at it this morning. I mean, it's kind of red and sore, but I'm okay."

"Still, as your doctor, I'd like to examine you."

She was gnawing on her lip. "Um..."

"Doctor's orders," I repeated.

"I, I just feel weird..."

"Come on, kiddo. No stalling. I've already seen it before. Take off your panties."

"Yes, Daddy," she whispered.

She put her bookmark in her book and set it inside. Then, she hitched up her skirt around her stomach. Her panties were simple, just white. She hooked the waistline with her thumb and pushed them down to her legs to her feet. She reclined in bed against a mountain of stuffed animals and then spread her legs open, nice and wide for her father.

I crawled in between them, making a point to put my hands on her inner thighs, spreading her legs even wider, just so I could see her pussy lips gape for me. I reached for them, spreading them with my fingers.

"Is it okay?" she asked.

"Give me a moment," I said, staring at her pussy. I could feel my cock growing longer and harder in my slacks, encouraging me to lie through my teeth if it bought me a ticket back into this delicious little cunt. "Sherry, I have some bad news."

"Oh, no, what?"

"Your hymen is broken, but because it was broken so quickly, I'm worried it's going to reclose."

"It can do that?"

"Yes, I'm afraid so, sweetie. You have to think of it like a body piercing. When you had your ears done, you didn't take the earring out right away, did you?"

"No. The girl at the mall said it could close up and get infected."

"Yes, that's right, infection. She was a smart girl, that mall worker. The same principle holds true for your vagina. See, when the hymen is broken naturally, during sex, the penis is usually inside the vagina for some time, keeping it open, but because I pulled out so quickly, I'm worried your hole could close back up and get infected."

"Well, what do I do?"

"I'm afraid I'm going to go ahead and put my penis back inside you."

"What, again?"

"Yeah, I don't like it either, but I think that would be safest."

"But it hurt so much the first time."

"It will start to hurt less the longer it's inside, but it will hurt a lot more if we leave your pussy how it is now. You may even have to go for that surgery you were so worried about."

Sherry looked nervous as she thought about it. "I don't know, Daddy. What we did, it felt so... wrong, you know? I mean, I feel all dirty, like I've been bad."

"Nonsense, Sherry. You're a very good girl. I don't want you to feel guilty. It was necessary before, and I'm afraid it's necessary again."

"Can we use the dildo this time?"

"No, I don't think that would work. See, last night when I put my cock in you, I realized your pussy is very small and tight. I'm worried the dildo, because it isn't as flexible as my penis, could seriously injure you. It's actually a stroke of luck that we didn't use it, but to be safe, I think I'd better just use my cock again."

She bit her lip. "Daddy, you wouldn't lie to me, would you?"

I looked her right in the eye and said, "Never, baby."

She gulped. "Okay, Daddy. You can put it back in me."

"There's a good girl."

I first took out the lubricant I had stashed in my pocket. Sherry seemed to question it with her eyes, and then I started to undress in front of her, taking off my tie and unbuttoning my shirt. My pants were next. I pushed them down, followed by my boxers, and my cock sprang free. It was already hard. I could barely contain my excitement. I crawled on the bed, coming closer.

"Wait, Daddy," Sherry said, looking at my cock. "Um, before we start, how long are you going to put it in this time? Just for a minute, or are you going to keep it in longer, and are you going to push it in and out?"

"I might have to keep it in for a little while longer than last time, and yeah, I'm going to have to push pretty hard to make sure your pussy hole is properly bored."

She frowned as she sized up my thick cock. "Would it be okay if I put my hands over my eyes and didn't watch? It makes me feel dirty."

"Here, I have a better idea." I took her hand and lifted her up to her knees. "Why don't you turn around and put yourself on all fours? Then you won't see anything."

"Like a dog?"

"Yeah, sure, just like a dog."

"Okay," she said, turning around carefully, putting her hands down on the bed, arching her back, her cute little ass sticking up in the air. "Like that?"

"That's perfect," I said. I squirted some lubricant on my shaft and massaged it in, staring at my daughter's pretty pussy sandwiched between her thighs. Fuck, this was going to feel good. "Ready, pumpkin?"

"I guess. Just not so hard like last time."

"Of course not, baby."

I crawled closer and put the head of my cock right up against her pussy lips, prodding. She wiggled, and then I slowly pushed forward, groaning as my cockhead popped inside her. Sherry yelped.

"Ow!"

"Fuck, you're so tight," I mumbled.

"What, Daddy?"

"Nothing, pumpkin. Daddy's just having a hard time fitting his cock into your cunt."

"Why do you use such dirty words, Daddy?"

"You're mother's filthy, whore mouth corrupted me. Now, hold on."

I took her hips and then in one hard thrust, rammed my cock all the way into her tight little pussy. She squealed.

"Not so deep, Daddy, it doesn't fit!"

"Sorry, kiddo."

I pulled back and pushed right back in, just as hard, making her whine.

"Ow! Daddy, stop doing that!"

I started to get a rhythm going, sliding in and out of her pussy, not going too deep. She was making little wincing faces, her nose crinkling up, her mouth hanging open to breathe. I began watching my glistening cock slide in and out of her.

"Doing okay, baby?"

She turned her head around and I saw her sad, glossy eyes. "Don't push it in so deep. It hurts when you do that."

"Like this?" I asked, giving her a hard thrust that rocked her body forward.

"Ow! Daddy, you're mean!"

"I only want the best for you, pumpkin," I said.

She turned back. My hands roamed over her hips and her ass, hitching her skirt up higher. I spread her cheeks as I watched my cock work in and out of her cunt. Then I reached around her thigh, touching her little clit. I began massaging it with my fingertips. She let out an exhale that sounded like a moan.