Sherry's Cherry

- Fair warning, this story contains some manipulation and reluctance, as well as some ludicrous plot mechanics. And unless you're a glutton for punishment, I recommend you skip the "extra scene" after the ending. Thanks to my volunteer editor _penny_ for all the help. All comments are welcome. I hope you enjoy it. -

"Daddy, can I talk to you?"

I looked up from my desk, pushing my glasses up my nose. My daughter Sherry was standing in the doorframe, still wearing her Catholic schoolgirl outfit, a white blouse and a checkered mini-skirt. Her long legs ran all the way down to her bare feet. She was bending her toes against the hardwood floor, looking nervous. She brushed her auburn hair out of her hazel eyes, staring at me. I hadn't even heard her come home.

"Sherry, it's not a good time. I'm buried in paperwork. Can we talk over dinner? Will you have something delivered?"

I considered the matter closed and returned to my computer monitor. I had taken the day off for this very reason; to catch up. I don't know where the last eight hours had gone, but joining a new medical practice had me up to my ears in work.

"Daddy, it's kind of important," Sherry said. "Please, five minutes?"

I sighed, leaning back in my chair, taking off my glasses and rubbing my nose. I needed a break anyway. "All right," I said, looking up at her and putting my glasses back on. "What's on your mind, kiddo?"

Sherry came all the way into the room, looking very nervous. She sat down in the chair on the other side of my desk, crossing and uncrossing her legs, looking around at the bookcases as if she'd never seen them before.

"Sherry?"

"Um," she said, "okay, I kind of have a medical question."

"Are you feeling ill?"

"Well, no, not really, I think."

"Are you in pain?"

"No, not right now."

"Sherry, I love you, but I don't have time for twenty questions. What's wrong?"

"It's a personal thing, like... a... feminine question, you know?"

"A feminine... oh!" I said, sitting up in my chair and clearing my throat. "Oh, okay. Um, all right, that kind of question. Well, I know we've never talked about sex, but you're 18, I figured you already knew everything you needed to know. Doesn't TV teach you this sort of stuff? Oh, god, tell me you're not pregnant. How the hell do you get pregnant at an all girl's school? Why didn't you tell me you had a boyfriend? Do I know him? It wasn't a priest, was it? God, I wish your mother was here, but she's probably still in Reno... with my brother. That bitch."

"Daddy, stop."

"You're right, she's not a bitch. She's a whore."

"Daddy!"

"Sorry, I didn't mean to speak ill of the undead. I'm just rambling because I'm nervous. How long have you been pregnant?"

"Jesus Christ, Daddy, I'm not pregnant! I'm the exact opposite of pregnant!"

"The opposite? Oh, my god, you had an abortion! Well, that's your choice. You know me, conservative at work, liberal at home."

"Geez, Daddy, I'm a virgin!"

I paused. "Oh."

Now, while my daughter did have a certain sex appeal, she was also what one might colloquially call... unkempt. I'd never seen her wear makeup---she claimed animal cruelty or something---and she refused to use any sort of hair product, so her hair was always a mess. She was the type who would rather read a book than go out with her friends, probably because she didn't have any friends. But she did have assets, which I don't even think she knew about, like curvy hips, a very firm behind, and plump breasts. She was a very late bloomer. Suffice it to say, I wasn't surprised she was a virgin, but I wouldn't have been surprised if she wasn't either.

"Okay then," I said. "I'm confused. What, uh, what did you want to talk to me about?"

She took a deep breath. "I sort of have this... problem. Like... down south... with my, you know, my... vagina."

"Oh! Now I see. I'm sorry. I was... okay. Same page now. Go on."

She nodded, gulping. "See, um, I was talking to my friends at school..." She had friends? "....and they were saying their periods only last a few days."

"Okay," I said. "Do you want me to get your mother on the phone?"

"No, Daddy. That would be even more awkward, and this is already awkward enough."

"Right, sorry. Go on."

"Anyway, my period lasts like, seven days, sometimes ten."

"Okay."

"Yeah," she said. "So, yeah, that's it."

"Is that what's bothering you?"

"Yeah."

"Well, is ten days your usual length? Or did this just start?"

"No, ever since I got my period when I was 15, it's been that long."

"Your period started at 15?"

"Yeah. Is that bad?"

"No. Many girls are late bloomers. It's fine. Ten days is longer than average, but it's not totally abnormal."

"But I also get really bad cramps and I get bloated and sick and stuff."

"Well, that's definitely common."

"I know, but my cramps are, like, severe and painful. Most days, I just come home and lie down because it hurts so much."

"Oh. I didn't know that."

Sherry stared at me. "Of course you didn't. You're always at work. You're never here when I need you."

That hurt. When your daughter tells you you're a bad father, it's like getting punched in the gut. "I'm sorry, kiddo, but you know this big house, you know that hybrid car you're driving, you know the food you eat, you know your bloodsucking mother's alimony? My job pays for all that."

"Well, maybe I'd rather be poorer and have a daddy who spends more time with me."

I sighed. "Look, I know when I was working at the hospital, I was never around. Jesus, it cost me my marriage, but things will be different now, just as soon as I'm situated at this new job. I promise, okay?"

She nodded. "Okay, but what about my problem?"

"Well, I don't know what to tell you, really. If you were my patient, I'd refer you to an OB-GYN."

"What's that?"

"A gynecologist, a vagina doctor."

"Ew, no way," she said. "I don't want some stranger looking at me while I'm naked, especially a boy doctor."

"There are female doctors, lots of them."

"That still makes me feel weird."

"Honey, I'm a doctor, not a psychic. I can't diagnose you if don't examine you."

"You mean you want to see me naked?" she asked, her eyes growing larger.

"Whoa, no! That's not what I meant. I meant I wouldn't be qualified to examine you. You need a gynecologist."

She frowned. "So you don't know anything about vaginas?"

I laughed nervously. "Not unless you count hands-on experience."

Sherry stared at me.

"I'm sorry," I said. "That was a very inappropriate thing to say. I'm just nervous."

"Me too," she said, "but actually, Daddy, I think I would be more comfortable if you examined me."

"Pardon?" I said. "Sherry, I'm your father. I don't think I'd be comfortable with that."

"But you take care of me when I'm sick."

"That's a little different than seeing you naked and looking at your private parts."

"Don't you examine girls where you work?"

"Of course, but it's different when it's a stranger."

"See, it's the opposite for me. I'd feel more comfortable if you saw me naked, because I know you would never have any, you know, sexual thoughts, since you're my daddy."

I gulped. "Well, of course not."

"So, will you do it? Will you examine me? And then if I really need an... OB-XYZ or whatever, I'll see one."

I rubbed my face. "You're sure this isn't going to make you feel uncomfortable?"

She shook her head. "No. And after my last period, I'm scared something's wrong with me. Next month is going to be even worse. Please, Daddy?"

"All right, kiddo," I said with a sigh. "But we're going to be very clinical about this, okay?"

"Okay, just tell me what to do."

"Why don't you go into the bathroom and take off your skirt and panties and wrap a towel around your waist? Come back in when you're ready."

"Okay. Thanks, Daddy."

Sherry left. I took a few breaths to calm myself down. This was highly irregular. It took me several minutes to clear off my desk. I stacked all the files into a box and put it aside. When I turned around, Sherry was back, wearing her white blouse and a white towel, her calves and feet sticking out at the bottom.

"I'm ready."

"Okay, have a seat on the desk."

While Sherry got situated, I went into the bathroom and scrubbed my hands. I also put on my white lab coat. Then I dug through my supply of stolen medical supplies, taking a pair of skintight latex-free gloves. They were bright blue. I came back to my daughter, who was sitting on my desk, her feet wagging nervously.

"Last chance," I said, coming around the desk. "You're sure you want to do this?"

"Yeah, Daddy. I trust you."

"Okay. I want you to lie back on the desk. Put your feet up on the edge and spread your legs, okay?"

"Okay."

My daughter reclined slowly, bringing her legs up, her heels on the edge of the desk, her toes gripping the wood. As her legs spread open, the towel rode up her waist, exposing her pussy, her very bald pussy. There wasn't a single hair to be found. I could see everything, her little clit, her pussy lips, even her asshole.

"Honey, have you always shaved yourself down here?"

She lifted her head to see me. "No. The girls at school made fun of me, so I started shaving about a year ago. That's not causing the problem, is it?"

"Well, no, it's just a matter of taste, I guess." My daughter really was naive about the world. Well, what did I expect? I sent her to an all girls' school, with nuns, and she was a bookworm.

"Is it easier to see my vagina without the hair?" she asked me.

"I haven't started the exam. I'm just asking questions."

"Okay. Does it look okay shaved?"

"Yes, it's fine. Let's just move on."

I sat in my office chair, face level with Sherry's pussy. I was going to have to touch her. It made me feel terribly guilty for some reason. I don't know why though. It's not as if I was doing something inappropriate, not including my thoughts...

"Honey, I'm going to have to spread your vaginal lips apart, okay?"

"Okay."

"So I'm going to touch you, all right?"

"I'm ready."

"Okay." I touched her pussy slowly. Her soft, puffy skin yielded to my fingers as I spread her lips open, examining her hole, or where her hole should have been. Her hymen was completely covering her opening, save for a very small notch, smaller than the circumference of my pinkie. "Sherry?"

"Yes?"

"Do you ever examine yourself with a mirror or anything?"

"No, not really. I mean, I look down there, but... you know."

"Do you use tampons or pads on your period?"

"Pads."

"Do you masturbate?"

Her head lifted up. "What?"

"I know it's personal. I'm just trying to get a complete picture here. Do you masturbate? It's not wrong if you do. It's very normal. In fact, if you don't, that may be part of the problem."

She put her head back down. "I guess... I rub my hand on top of my panties sometimes, but only sometimes."

"Do you ever put your fingers inside?"

"Daddy..."

"Honey, just answer the question."

"No. It hurts a lot when I try to put anything in there. My hole is too small, isn't it? I was scared that's what you were going to say. I know it's small because it hurts so much if I even put my pinkie in there. I don't even like to touch it."

"Yeah," I said heavily. "Sherry, it looks like you have a microperforate hymen. It's not uncommon though. It just means the opening didn't fully form. But that's why your periods last so long, because you're bleeding slowly. The stomach pain is probably because you're retaining some of that blood."

I stood up, pulling the towel down. She sat up, closing her legs, looking up at me. "What do I do?"

"Well, I really think you should see a gynecologist."

"And what's he going to say?"

"He, or she, will tell you that you may need surgery to widen the opening, just to be on the safe side."

"Surgery?" she said, looking sad, as if I had just told her she had three months to live.

"It's not that bad," I said.

"What will they do?"

"Well, they'll probably put you to sleep, and then cut the hymen open, drain any fluid..." I stopped because Sherry's head was down. "I know it's scary, but you'll get through it."

"It's going to hurt?"

"Probably, yes."

"And all those doctors are just going to be standing around my vagina, cutting me open while I'm naked?"

"I guess, yes."

"Boys and girls?"

"Yes, probably."

She looked up. "I can't do that, Daddy. You know I'm shy. I don't even like to talk to boys. I can't be naked around them."

"I'm a boy."

"You're not a real boy. You're my daddy."

"Baby, this is a health issue. It's not about modesty."

"Isn't there a better way? What else can I do?"

"Short of losing your virginity the old fashioned way, there's nothing else."

She bit her lip. "So if I had sex with a boy, I'd be better?"

"Yes, a penis would tear through your opening, and the hymen wouldn't be an issue anymore."

"I don't know any boys though," she said, looking up at me.

"I'm a boy," I reminded her.

She stared at me in shock. "You mean... you would...?"

I hadn't actually meant it like that, but the thought of it took over my head for one brief moment. I could see myself just fucking my own daughter right here on this desk, my cock sliding in and out of her pussy, taking her virginity, her blood smeared across my shaft.

"What? No, of course not. I didn't mean it like that. I was just... look, there may be another way. I can buy you a, uh, feminine pleasure toy."

"A pleasure toy?"

"A dildo, Sherry. It's a plastic penis," I said. "Then you can do it yourself."

She bit her lip. "I don't know how I feel about putting things up my vagina."

"Sherry, I don't know what the alternative is you're looking for."

"Well, it's just, I was trying to save my virginity until I was married, and my wedding night, the honeymoon, like in the movies. It's my dream."

"Oh."

She looked so sad, her face downcast. I hated seeing her like that.

"Cheer up. Having your hymen broken isn't really like losing your virginity."

"It's not?"

"No. Most girls' hymens are broken long before sex anyway. What you'd be doing is just paving the road for your future husband. Then when the time comes, there won't be any pain, and you can just enjoy it. Doesn't that sound like a better honeymoon?"

Sherry started to smile. "Yeah, I guess you're right."

"Good."

"If we buy one of those toys," she asked meekly, "will you do it?"

"Yeah, I'll buy it for you," I said. "No problem."

"No, I didn't mean buy it. I meant, will you, you know, put it in me?"

"Um, pardon?"

"Daddy, it hurts so much whenever I try to put my finger in. I don't think I can do it. You know how bad I am with pain. I just shut down. Will you do it?"

"You want me to put the dildo in you?"

"Yeah. Is it gross to ask you?" she asked, looking nervous.

I have to admit, it was a little gross. She was my little girl. I raised her. And now I was going to penetrate her... with a dildo? It didn't seem right. Of course, I argued if I was a surgeon, wouldn't I operate on her to save her life? Well, then the answer was yes, of course. So, wasn't this sort of the same thing?

"Sure, honey," I said, giving her a smile. "I know this is hard, but I'll be your doctor for this. I'll rupture your hymen, and we can put this whole thing behind us. Sound good?"

She nodded happily. "Yes. Thank you so much." She jumped up and hugged me with one arm while she held the towel around her waist. "When do you want to do it?"

"Whenever you do."

"How about after dinner?"

"Tonight? Well, okay..."

We ordered some take out, which I went out and picked up, with a quick stop at the sex shop. You'd be surprised how awkward this kind of thing could be...

"One dildo please."

The clerk just looked at me for a moment. He pointed at a rack with dildos hanging like sausages in a butcher's shop. One of them was as big around as a table leg, and as long. "Do you want the extra large mocha stretcher?"

"Shit, no! For fuck's sake! Just give me that one there, second shelf, the flesh-colored one. Goddamn..."

He took it down, a sculpted penis about eight inches long, still in its packaging container. It actually looked a lot like my dick, though my dick had a pair of testicles attached, thank you very much.

"Here you are, sir."

I handed him my credit card. "It's not for me, you know."

He looked up. "Yeah, I haven't heard that one before."

"It's for my daughter, smart ass."

"Okay, I've definitely never heard that one before."

I left the store and went back home. My daughter was looking nervous. I didn't blame her. I felt the same way. We ate Chinese food in silence. I couldn't even think about doing any more work tonight, certainly not after I took my daughter's cherry with a dildo.

"So, um," Sherry said, "I'm gonna take a shower, get ready, you know?"

"Sure, whatever you want to do."

"Okay. Can I see it first though?"

"The dildo?"

"Yeah."

"Okay."

I went back to the living room where I'd left the bag. Sherry was peering over my shoulder. I took out the package and held it up. Her eyes flew open when she saw it.

"That's it?"

"Yeah. What were you expecting?"

"I don't know. I didn't know they were that big. They're not that big in real life, are they?"

"Well, most men are around six. This is eight. It's only two inches difference."

"Two inches that's going into my vagina."

"I won't push it in all the way. I need a handhold."

"Still... it's kind of thick around."

"Oh. I guess it's a little above average."

She looked up at me. "Why didn't you get me below average? It's already going to hurt."

"Honey, I didn't go browsing. I just picked one."

"Well, why this one?"

"I don't know. I guess it reminded me of me, so I just picked it."

She was staring straight at me. "You got me a dildo that looks like your penis?"

"Wait, no. That came out wrong. I just meant that it was familiar, not that I wanted my penis in your... er, look, do you want me to return it and get you a different one?"

"No, it's okay. I just feel really nervous. Can I touch it?"

"Yeah, of course." I opened the packaging and took it out, handing it over. She had a crooked look on her face.

"It just looks so much bigger than my vagina."

"Your vagina will stretch. That's its job."

"And we're just going to put in and take it out real quick?" she asked, looking up at me.

"Pretty much."

"Okay, I guess. I'm going to take a shower. Where are we doing it?"

"The office."

"Not my bedroom?"

"We should try to be clinical about this."

She nodded. "Okay. I'll see you in there in a half hour, okay?"

"Okay."

In my office, I tried to relax. I even lit a candle. I don't know why. I just didn't want my little girl to remember the whole event in a negative light. Still, the whole idea of shoving a dildo into my daughter's pussy, popping her cherry, was exciting me. I kept grabbing my crotch, adjusting my cock in my slacks. I even began fantasizing about doing it, plotting. What if I put a towel over her waist like earlier and substituted my cock for the fake one? Would she know? How could she?

Geez, that's terrible to imagine. Of course I wasn't going to do that. I mean, she'd know the minute I grabbed her hips with both hands and started pounding into her. Look, honey, no hands! There was something wrong with me, thinking like this.

"Daddy?"

I spun around. I had almost expected her to be wearing lingerie. She had on sweatpants and a t-shirt, but they did hug her hourglass frame, and I could see she had taken off her bra.

"I'm ready, I think."

"Okay. Do you want to jump on the desk?"

"Um, can I just see the thing again?"

"Yeah, sure," I said, taking the dildo off the desk and handing it to her like it was the TV remote.