Sherry's Cherry

She bit her lip as she stared at it. Then she sat down on the leather sofa in my office, her feet curling up under her butt. Her hand squeezed the dildo's shaft.

"It's so hard."

I sat down next to her. "You were expecting it to be soft?"

"No, I don't know what I was expecting. I've never seen a real one."

"Would you like to?" I couldn't believe I just said that. It was like a compulsion, like I had no control over my mouth.

"What, um, what do you mean?"

I could have backpedaled right there, said something about a diagram on the internet, but god help me, my cock felt so strained, I just wanted to pull it out and see the look on her face. And, fuck, I was horny thinking about this whole scenario.

"I know this has been uncomfortable for you," I said, "so if that's bothering you, I can show you mine."

Sherry's took a big gulp and licked her lips. I think she was speechless. I chuckled to break the silence.

"Sweetheart, I'm sure you have a lot of questions. All I want to do is answer them, and sometimes a picture is worth a thousand words, so if seeing my penis would put you at ease, I just want you to know, I'll do that for you."

Sherry looked a little confused, trying to work out how I had turned that around as if she had asked to see it. "I don't know. That seems kind of, you know, um, weird?"

"Oh? I examined you. I thought it would be fair to give you the same chance. Clearly sex education isn't an integral part of your curriculum at school. I guess I should have sent you to public instead of private."

"I, I just meant because you're my daddy and stuff, it might be weird to see your, you know, thingy."

"Nonsense. Come over here."

I patted the sofa cushion and my daughter scooted a little closer. I could almost hear her heart racing inside her chest, her perky tits straining against her t-shirt with each breath, her nipples hardening. Really, I couldn't believe I was doing this. But I reached down to my slacks, took hold of the zipper, and pulled open my fly. My daughter's eyes were saucers as she watched me reach in and fish around for my cock. I grabbed my semi-hard shaft and pulled it out into the open. It grew harder and harder as I looked on my daughter's stunned face, the way she just stared at it. Soon, my cock was standing straight up like a flagpole, and just as hard.

"See, that's not so different from the dildo, is it?"

She glanced away from my cock for one second to look at the dildo in her hand.

"It's, um, it's pretty different."

"It is?" I said. "What's different?"

"I don't know. Yours looks so much more... real, and it looks longer and thicker too."

"Here, let me see." I took the dildo from her hand and she watched as I placed it right beside my cock. "Hmm, not too different."

"No, see," she said, pointing, "yours has veins and stuff, and the head of yours is bigger."

"Yeah, but they're both circumcised, about the same length." I squeezed the dildo in one hand and squeezed my cock in the other. "The only real difference is how they feel."

Sherry looked up at me. "How does yours feel?"

I smirked. This was almost too easy. "It's hard to describe. Here, why don't you touch it?"

"Oh, no, no, that's okay," she said shyly, turning her head. "That's okay."

"Sweetheart, I touched you."

"You had to. I'm not a doctor or anything. I shouldn't even be seeing this."

"Sherry, look at me," I said. She looked. "This is no different from what I did. You're learning. Go ahead. Touch it."

She was chewing on her lower lip as she lifted her hand. Her fingers came closer and closer, until the tips bumped into my shaft. She instantly pulled away, but I gave her an encouraging look and she reached out again, touching my cock. She prodded it with her nails.

"Wow."

"What do you think?" I asked.

"I don't know."

"Put your hand around it," I directed.

"Why?" she whispered, looking at me.

"So you can feel it properly. Put your other hand on the dildo."

"Um, okay."

She took the dildo with her other hand first, and then her right hand slowly came around my shaft. She did not squeeze; she just held it loosely in her palm.

"Squeeze it," I told her.

"Okay," she said.

And then she squeezed. I felt the pressure of her fingers all around my cock, and fuck, it felt good.

"That's good," I said, watching her hand. "Why don't you try to stroke it a little, see how the skin moves?"

"Um, how do I do that?"

"Just hold on tight and slide your hand up and down."

I put my hand around her hand, sliding it slowly up before I moved it back down. I took my hand away and she followed my lead. I couldn't believe my daughter was doing this. Somehow, I expected her to stop me, to tell me this was not at all right, that she knew better than to be touching her father's cock. Instead, I just watched her hand move up and down my shaft. All the while, she kept adjusting her fingers, changing her grip, like there would be a test on this later.

"What do you think?" I asked her.

She immediately stopped, taking her hand away and looking up at me. Her cheeks were rosy red. I guess she had been blushing, but I had been too preoccupied to notice.

"Um, it feels much different from the dildo."

"How so?"

"Well, yours is really hard on the inside, but it's sort of soft on the outside, like it's flexible. The dildo's just... it's like a piece of metal or something."

I smirked. "Which one do you like better?"

"Huh? Oh, I don't know."

"It's okay, sweetheart, you can answer."

"Um, well, I mean, yours feels nicer in my hand, but I mean, you know, I could never, um, yeah..."

"What?" I said, but I knew what she meant. "Oh, you mean use my penis to rupture your hymen?"

She gulped with her red cheeks. "Yeah. I mean, of course not. So, this dildo thingy will do."

"Well, sweetheart," I began, "there's really no difference between the two."

"Um, huh?"

"What I mean is, we're going to have to lay you down and put something long and hard into your pussy, for medical reasons of course. If you don't like the dildo, I don't mind if you want to use my cock instead."

Sherry's mouth fell open. This time, I let that awkward silence hang until she spoke. "But, but, but, Daddy, isn't that like, like sex? We can't do that."

"Well, no, honey, it's not sex, actually," I said. "See, with the dildo, it's really just a form of masturbation, and if I use my penis, it's the same thing, just with a different tool. The fact that the tool is attached to me doesn't necessarily make it sex."

"Um, oh," Sherry said. I wondered if she knew I was bullshitting my way through this. "What makes it sex then?"

"An orgasm," I explained. "See, an orgasm is when a man or woman experiences an intense moment of pleasure. A man typically ejaculates, and a woman releases fluids. Most people just call it cumming."

"I, I know what orgasms are, Daddy. But I thought they happened at the end of sex."

"See, that's a medical misnomer. Certainly, I would say, uh, thrusting in and out is a form of sex, because it directly leads to cumming, but in our case, by simply inserting the penis into the vagina for the sole purpose of penetration, it's not technically sex."

Sherry stared at me blankly for a moment. She was probably thinking I was the dumbest doctor on the face of the earth if that's what I thought, but my daughter was also very obedient. So all she said was, "Okay, Daddy."

"Good girl. So, why don't we get you on the table, and since you prefer my penis to the dildo, I'll go ahead and penetrate your vagina, and then we can put this whole mess behind us."

She lowered her eyes. "You're going to put your penis inside me?"

"Yes. Isn't that what you just said you wanted?"

"Um, well, I don't know. Maybe we should just use the dildo."

"Sweetheart, you don't have to feel shy. I'm your father. I know best."

I stood up in front of her, my long cock pointing in the air over her head. She looked up at it with big eyes, like it was a weapon descending from the heavens. I held out my hand to her and she took it, standing up, and then I walked her over to the desk.

"Ready to take off your clothes?" I asked her.

"Um, okay. Just the bottoms, right?"

"Actually, I think we should take off the top too."

"Why?"

"Well, sweetheart, you may feel a little bit of pressure when I enter you, and if you play with your nipples, it might distract you from the pain."

"What will that do?"

I paused. "You've never played with your nipples before?"

"Well, they're really sensitive, so I don't like to touch them."

"Okay, well, today will be a lot of firsts for you. Just try to play with them during the penetration. You may enjoy it. Come on. Hop up."

I put my hands on her waist and lifted her butt up onto the edge of the desk. Her legs dangled over the side. She nervously kicked her heels against the wood while her eyes darted back and forth around the room, but they always came back to my cock.

"Come on, let's take this off," I said, reaching for the bottom of her shirt. I peeled it up her body, over her head, exposing her milky white breasts, untouched by sunlight, her pink nipples bright in comparison. She shyly crossed her arms over her chest, trying to block my view. "Now, your pants, sweetheart."

I slid my hands down her curved sides, slipping my fingers into the waistband of her sweatpants. She propped herself up with her hands and lifted her butt off the desk, once again revealing her beautiful tits while I pulled her pants down. I took them off at her feet and then I touched her calves, running my hands all the way back up to her thighs, reaching for her panties. She repeated the maneuver so I could peel her panties away from her pussy. The delicate scent of her cunt filled the air around me.

I stared at her as she sat on my desk, naked, looking so full of trepidation. Then I began to undress myself, starting with my tie, loosening it and pulling it over my head. I unbuttoned my shirt slowly, all while I stared at her. Her lower lip was trembling, her eyes constantly jumping down to my hard cock. She crossed her legs, as if to protect her little pussy from an invader.

I tossed my shirt on the floor with the rest of our clothes and then unbuckled my belt. I could hear Sherry breathing heavily. I opened my pants and they fell down. I pushed my boxer shorts after them, freeing my cock. Sherry's eyes grew a little larger when she saw my balls hanging between my legs. I kicked my clothes off to the side with the rest of the pile.

"Ready, kiddo?"

"Um, um, I guess."

"Here, why don't you scoot a little closer?" I stepped toward her, my cock bumping into her knee, and put my hand on her lower back, bringing her ass to the edge of the desk.

"Uncross these for me," I said.

I slid my fingers between her thighs and pried them apart. She opened up her legs to me, her shaved cunt exposed. I stepped closer, right in between her legs. My cock stabbed her tummy."

"Oh..." she murmured.

"Lie back," I said

She went ahead and put her feet on the edge of the desk, spreading her knees far apart as she rested on her elbows. She looked down at my cock hovering over her pussy.

"Daddy, I'm really scared. This feels like it might be like sex."

"It'll be fine, Sherry. We're just going to break the hymen, and then I'll pull right out. It's not sex."

"I know, but you're a boy and I'm a girl, and---"

"You said I wasn't really a boy, remember?"

"I, I guess..."

"Good girl. Now, let me look at your pussy to see if you're ready."

I reached down between her legs, moving my aching cock out of the way so I could see properly. I just wanted to ram into her, fuck her so hard she flew off the desk, but even though I was taking advantage of my little girl, I justified that it was a necessary medical procedure, and I was going to try not to enjoy it too much.

My fingertips touched her pussy and I caressed her slit. She was a little warm, but I needed her cunt to be red hot, ready for sex. After all, she was my little girl, and I didn't want to hurt her... much.

"Baby, you're not ready yet."

"I'm not? Does that mean we're not going to do it? Okay, I understand."

"No, kiddo, it just means I'm going to have to get your pussy ready. Have you ever had anyone kiss or lick your pussy?"

Her eyes flashed. "No way!"

I laughed. "Well, it'll be easier to penetrate you if I go ahead and lick your pussy a little, all right?"

"Um, um, I don't know. That seems kind of gross. I mean, I pee out of there, you know? It's not the cleanest, is it?"

"You just showered, it'll be fine."

"I know, but still..."

"Relax, pumpkin. Daddy's at work."

I knelt down and brought my face between her legs, inhaling the scent of her cunt. Her clit was poking out just a little. I kissed it before glancing up at her. She was watching me, holding her lower lip between her teeth. Then my tongue rolled out of my mouth and I licked her slit from bottom to top, crossing her clit again. Sherry held her breath.

"Um, um..."

"How does that feel, baby?"

"Weird," she said.

"Let's try it a few more times."

I licked against her pussy, pressing my tongue into her hymen, feeling the little hole that was about to become much bigger. She whimpered as my tongue worked. I moved my mouth up to her clit and closed my lips around it, sucking and licking.

"Oh," she mumbled. "Oh, god."

"There you go," I said. "Feels good?"

"I guess, a little, yes. Feels wrong too though."

"It's only so your pussy is relaxed, like stretching before a workout, and stretching is what you'll be doing. I need all the room I can get."

"But if I went in for surgery, the doctor wouldn't lick my pussy, would he?"

"He might, or he might stab a very large needle into your pelvis to administer an anesthetic. This way is easier, huh?"

She gulped, nodding, and I returned to my job, licking her little pussy, sucking on her engorged clit.

"Oh, Daddy," she said, letting out a little moan. "It's making me feel really good. I've never felt anything like this before. I think, I think I'm having an orgasm. Am I having an orgasm?"

"If you're talking through it, probably not."

Sherry kept moaning quietly as my tongue worked her clit over. She was as ready as I could make her. I stood up between her legs again, my cock even harder after tasting my daughter's cunt. I took a small bottle of lubricant and spread it over my shaft. Sherry's nervous eyes seemed to realize it was time.

"Daddy, I really think we should use the dildo."

"Pumpkin, you can't change the surgeon's scalpel in the operating room. This is what you wanted."

"Well, I didn't exactly ask for it. It just seems so wrong since you're my daddy."

"I told you, it's not sex. Just try to relax. I don't want you thinking about anything other than happy thoughts. Here, you haven't even started playing with your nipples. Go ahead. Touch them."

She nervously put her hands on her breasts, caressing them, her thumb stroking over her long nipples. I had a feeling it wasn't going to help much. I stepped into position, my big cock right over her pussy. Her toes were gripping the wood on the desk as she watched. I took my shaft in my hand and angled it at her tiny hole, slapping her cunt once with the head.

"Eek," she yelped.

"Haha, it's okay, honey, we haven't even started yet."

I gently nudged her hole with the head of my cock and her whole body tensed up.

"Daddy, I don't think I can do this."

"Baby, I'd hate to see you on a real operating table, with ten different men standing around you, all ready to cut your vagina open. And who knows what they might do to you while you're unconscious? You don't want that, do you?"

"No," she whispered.

"Okay, then be a good girl."

"Please, just go really slow."

"I think faster might hurt less."

"I don't care. I need you to go slow."

"Okay. You just try to stay calm and let me do all the work." I reached out to her cheek, stroking it once with my thumb. "Here, bite down if it hurts.

She parted her mouth slightly and I slipped the thumb in sideways, between her teeth. She closed her mouth on my thumb, her teeth pinching it. With my other hand, I rubbed the shaft of my long cock along her slit, grinding into her sensitive little clit. She kept her eyes on her pussy, watching me while her hands absent-mindedly played with her reddening nipples.

"Here we go," I said.

I held my cock steady as I pushed forward. My mushroom head spread her lips apart as it pressed into her hymen. Sherry immediately screamed, spit my thumb out of her mouth, and let go of her breasts to push me back.

"Ow, stop! Ow, ow, ow!"

I pulled back. "I haven't even penetrated you yet."

"Ow, shit," she said, holding her pussy with both hands, crossing her legs and rolling onto her side. "That hurt so much."

I put my hand on her bare hip and rubbed in a circle. "Kiddo, you knew it was going to hurt."

"Not that much," she whimpered.

"Okay, come on," I said, taking her hip and rolling her back over onto her back.

"Daddy..."

I grabbed her ankles in each hand and pulled her legs apart. She put her heels back on the edge of the desk, but she was holding onto her pussy for dear life. I grabbed my shaft and knocked on her fingers a few times.

"Come on, baby, we have to do this."

Her lower lip was trembling. "I don't think I can do it. I really don't. I think I'd better do the surgery."

"You'll regret the surgery. We've already come this far. Let me just put it in."

"I'm so scared though."

I rubbed my cockhead against her fingers. I wanted in her cunt so bad. I wasn't quitting without a fight.

"Baby, I'm worried about your health. We need to fix this now. Just let me shove it in hard and fast. It will only hurt for a moment. Then it will all be over."

"Daddy..."

"Pumpkin, it's your choice. It's either me or the scalpel. What's it going to be?"

Her eyes were watery, but she took her hands away from her pussy. I placed my cockhead right up against her hole.

"Okay, just close your eyes," I told her.

She nodded, putting her hands over her eyes. I took hold of her hips, held her firm, and then pulled her in as I shoved forward. My cock shredded through her hymen in one thrust, but her pussy was so small and tight, it was actually painful for me to enter her. I groaned loudly, but my daughter was screaming even louder.

"Oh my god! Daddy! Ow, Daddy!"

Her legs were off the desk, her toes spreading open as I spread her cunt open, her arms flailing and grabbing my chest. She was crying and whimpering as my cock hit rock bottom and I was forced to stop.

"Fuck," I groaned.

"Daddy, take it out! Take it out!" Sherry said as she sniveled and cried. "It hurts so much!"

"Oh, baby, I know it does," I said, looking down at my cock lodged all the way in my daughters cunt, the way her labia wrapped around my shaft in a loving embrace. "We just have to, um, make sure your hymen is completely ruptured."

She whimpered. "It is. It has to be. It hurts so much. Can you take it out now? Please, it hurts, it hurts."

"Baby, I can't take it out right away," I said, looking down. I pushed forward and she whined. "We have to leave it in a little longer."

"How much longer?" she asked, sitting up enough to look down at her pussy.

"Until it doesn't hurt as much," I said.

She frowned at me. "Daddy, this is sex, isn't it?"

"No, no, baby, of course not. See, I'm not even thrusting, am I? I'm staying very still inside your pussy. I just want what's best for you."

"But it's so big, it hurts. I can feel it in my tummy." She held her stomach, rubbing in a circle. "It's inside there. I can feel it. It's in way too deep. Can't you take it out now?"

"How about I take it out a little?" I said.