Emily's Confidence

Sometimes it's hard to believe my sister and I are even related. Charlotte is a gorgeous brunette with straight hair and flawless skin. She's 5'8" tall with these perky D cups, and obviously the boys were obsessed with her all the way through high school and college. She makes friends so easily, because she's confident and fun. Now, she's 28 and happily married to an equally gorgeous guy.

And then there's me. I'm a geeky, shy, virgin. I wear glasses, and I've got wiry, curly hair that I usually don't do anything with apart from trying to keep it out of my face. I'm 5'3", skinny, with no tits, no hips, no ass. I had braces and horrible acne all through high school.

All my life, I've compared myself to Charlotte, which obviously has done wonders for my self-esteem. But don't get me wrong - I don't resent her, not even a little. She's always been wonderful to me, and we love each other to bits. But just when I compare everything she has to the very little that I've got, I kinda spiral a bit. Or a lot.

This particular tale starts when I was in the middle of one of those depression spirals. This time, I was particularly resentful of the fact I was 25 and still a virgin. The furthest I'd been with a guy was been making out while drunk on a night out. And I wasn't exactly in a position to meet too many guys in my job as a receptionist in a plumber's office - it's pretty much a phone- and email-only job.

It's not like I'm a prude, though - I have a massive sex drive. At least once a week I'll go to work in a dress and no panties, just for the thrill of knowing I'm one strong gust of wind away from being exposed. I'm constantly watching porn and getting myself off, even on public transport and breaks at work. I think my friends are sick of hearing me (half) joke that I'd be a huge slut if I just had a chance. It's just, being shy and without any confidence, I couldn't approach guys, and I'm always second-guessing if a guy is actually into me, or just likes me as a friend. So I'm kinda my own worst enemy.

I was beating myself up about all that one night over dinner when my mom reached over the table, gently touched my hand and asked "Em, are you okay, honey?" Oh yeah, did I forget to mention I still lived with my parents? Just another medal in the Life Sucks Olympics.

I looked up at her and it took a second to remember where I was. "Hmmm? Oh, yeah, I'm fine. Just tired," I sighed.

"Come on, Em," Mom replied. "We know you better than that. What's really bothering you?" Neither of my parents could relate to how I felt; they were both really good looking, and got married when Dad was 23 and Mom was 21. They'd had Charlotte before either of them were my age.

I shrugged. "Same shit, different day, I guess."

"Language," was Dad's response, not even looking away from the TV. Funny how he was allowed to swear as much as he wanted, but it was still off limits for me.

I rolled my eyes. "Same STUFF, different day."

"Like what?" Mom nagged. This was already getting tiresome.

"Ugh! Like I'm a fucking loser who's never had a boyfriend and probably never will at this rate." I stared angrily at my plate, trying to stop the angry tears forming in my eyes.

"Emily, sweetheart, you're not a loser. You're beautiful and any guy'd be lucky to have you." At least Dad was paying attention now. Pity he was only talking in cliches.

"Yeah, you're right. That fixed everything. I don't know what came over me. Thanks, guys." I took a couple gulps of water and set the glass down a bit harder than I'd intended, causing a rather dramatic slam.

Now it was Mom's turn again. "So if it's bothering you so much, what are you trying to do about it? Are you on The Apps?"

"Jesus Christ, Mom, you don't need to capitalize it. No, I'm not on any apps. They're..." I sighed, exasperated. "They're not the place for virgins." Great, now my face was burning up with embarrassment. "Anyway, I'm sorry I brought it up. Can we drop it now?"

"I'd love nothing more." Dad was squirming in his seat. "But just know we love you."

"And if you ever want us to introduce you to any boys, you just let us know," Mom tried to joke.

"So long as he's not picky about where he sticks his dick, send him my way" was ALMOST my reply, but I'd already hit my limit of talking about sex with my parents for one lifetime. I just forced a smile and that's how we got through the rest of dinner. It helped that some politics story came on the news and got Dad all fired up.

Later that night, I was feeling pretty guilty about that whole conversation at dinner. I put my laptop down and went to find Mom. She was in their bedroom, doing some study. It was her last night at home before she had to go away for a week and do some sort of training course for her work.

I stood in the doorway and knocked. Figured I'd start with the obvious. "Hey, Mom. Studying?"

Without looking up, "Sure am."

I stepped into the room. "Just wanted to say I'm sorry bout before. At dinner." Like I had to specify.

She looked up, with a "go on..." look on her face.

"Like, I know it's dumb, but I compare myself to Charlotte all the time and she's just way more successful than I am, in everything. And then I see you and Dad all the time, and it's like, why don't I have what you all have? And..." I sighed and shrugged. "Anyway, I'm sorry for being moody."

Mom got off the bed and hugged me. "It's okay, sweetheart. I know it's hard, but trust me. These things have a way of working out, some way or another." She kissed my cheek. "You really are special and beautiful and your Dad and I both wish there was something we could do to help."

I know parents are supposed to say that stuff, but this time it did sorta help. Maybe I was just feeling extra vulnerable and needed to believe it this time. "Thanks, Mom. You're the best." I left her to her study.

I didn't see Dad until the next morning. He'd already taken Mom to the airport and was quickly finishing up his breakfast. He works as a builder, so he starts work pretty early.

"Morning," he said between bites of toast, not quite looking me in the eyes. I think he still felt super awkward about dinner.

"Morning, Dad," I started. "Sorry again bout last night."

"I know. It's okay, sweetie. I could've been more supportive, but I just never know what to say." He shrugged apologetically. I nodded and smiled. "I need to get to work now, but we can talk more after work, if you need." He kissed me on the forehead, grabbed his car keys and rushed out the door. "Bye!" he called just before the door closed behind him.

When I'm not in a funk, I treasure having the house to myself. But I was, so as soon as Dad left, I felt every bit of my loneliness. I ate my cereal in sad silence and gradually got dressed and ready for work.

Work was...work. Just another day scheduling and rescheduling the plumbers, and soothing irate clients who had already waited 2 hours past their scheduled appointment window. They always say they understand it's not my fault, but they need someone to blame, so they yell at the meek, faceless girl on the other end of the phone. But you get used to it after a while. There's always worse jobs for worse pay, I guess. What I'm trying to say is, panties and no masturbation for me that day. Just the usual 9-to-5.

I got home and, as usual, Dad was already there. "There's my beautiful girl," he called out when I stepped in. It was pretty safe to assume he was already a couple beers into his post-work routine. He always gets flirty with everyone when he's been drinking - not even his own daughters were safe. But he never means anything by it, really. "How was your day, Em?"

I followed his voice into the kitchen. "Hey, Dad. Yeah, work was fine, nothing too exciting to report." I poured myself a glass of water. "You?"

"Yeah, me too. Hey." He looked me up and down. "I've always liked that dress on you, sweetheart." He was still in his work clothes, sitting at the kitchen table, TV going in the background.

It was a basic black sundress with a daisy flower pattern. Semi-modest neckline, hemmed just below the knees. Business casual kind of thing. Like myself, it's nothing special. But I was still feeling needy after last night, so I took the compliment. "Aaw, thanks, Dad. It's nothing special."

"Unlike you," came the reply. "You know your Mom and I love you, right, Em?"

I finished my glass and set it down on the bench beside me. "Yeah, all right, I know."

"And you know we both think you're gorgeous?"

"Uh, I guess?" This was starting to get a bit intense mow. "Where are you going with this, exactly?"

"Your little outburst last night...I think I know what you need now."

"...Riiight..." I shifted uncomfortably, but remained fixed in my spot, my back leaning against the bench.

"You just need some confidence, Em. I'm sure you'd do fine on The Apps if you just felt better in yourself."

"Dad, I don't really wanna get-"

"But you reckon you can't go on there because you're a virgin." He started to blush, but he kept on, determined to finish this little speech he'd prepared. "So... What if you just had sex?"

I rolled my eyes so hard it took a second for them to focus again. "Oh gee, Dad, I'd never thought of that before! It's all so fucking obvious now!"

He stood up and walked towards me. Soon, he was like 2 feet away from me. My back was still against the bench. "And suppose I knew someone who'd be willing to do that for you? Be happy to do it, in fact?"

I frowned at him, not terribly enjoying seeing this new side of my father. "Umm..."

"It's a chicken-and-egg thing, isn't it? Can't date because you're a virgin. And you're a virgin because you can't date. So it's pretty obvious." He stepped closer again. "You need to be fucked. Don't you, Emily?"

"Language," I replied by reflex. Then I actually processed what Dad just said. "Wait, what?"

He stepped right in front of me, mere inches away now. "You need. To be fucked."

This...really couldn't be happening, could it? No. No way. I was misinterpreting this in a big way. "Dad, what the fuck?" I tried to lighten the mood with a joke. "Why, you got someone lined up for me?" I smiled up at him.

He placed a finger on the front of my dress, just on the neckline. "You could say that, yeah. If you'd like...dear old Dad might be willing to help." He smiled. It was a weird combination of awkward and confident.

Again, I had to ask, "What the fuck?! Jesus Christ, Dad. You and Mom never gave me 'The Talk,' and now...this?" I tried pushing him away, but I was 5'3" and barely 100 pounds. He was almost 6'2" tall and almost 200 pounds, so he stayed right where he was. Towering over me, his finger tracing the neckline of my dress.

"It's just a suggestion, Emily. Just one idea I've come up with." He put his big hands softly on my hips. "Take it or leave it, it's up to you."

I couldn't fucking believe this, so I told him as such: "I don't fucking believe this." My face was red with...embarrassment. Right? Surely. I was breathing more heavily, and squirming while Dad gently held me in place, pinning me against the kitchen bench. That warm, tingly feeling coming from my crotch? Totally irrelevant. There was no way I was, like, turned on by this.

Just because this was the most direct any guy had ever been, the least confused I'd been about a man's intentions I'd ever been in my life. All that didn't mean anything, because this was my fucking father!

My fucking father, who was now lifting me up on the bench like I didn't weigh a thing. He sat me down and ran his hands up and down my sides. Just lightly caressing me, nothing inappropriate...apart from what he'd said to me mere seconds ago.

"You don't have to decide now, pumpkin," he almost whispered as he watched his hands roam my body. "Just know that the offer's on the table, and that Dad's..." He let the facade drop now - his right hand trailed from my side right down to my crotch, pressing his hand and my dress and my panties against my warm, moist pussy. "...here for you," he finished.

There was no way this was real life. This kind of shit only happened in bad erotic fiction. But here I was, propped up on the kitchen bench with my Dad molesting me, and my body undeniably enjoying it. Still, that didn't mean I was so desperate that I'd actually go along with this bullshit, did it? I wasn't so pathetic a loser that I'd let my drunk, old father take my virginity...was I?

Before my brain could come to its own conclusion, my body leapt ahead and answered. I heard myself moan and felt my legs spread to my father's touch. I couldn't believe I was giving in to him, taking him up on his ridiculous, adulterous, incestuous offer. But my mouth was open, my eyes locked on his, my pussy was wet, and my legs were open. This was happening. I was letting it happen. I felt myself nod.

With his right hand still in my crotch, he reached behind me with his left and deftly unzipped my dress. I helped him slide it off my shoulders. It fell down, exposing my bare torso to my Dad. When your tits are this small, you never need a bra. My small nipples were already hard. He looked at them, not disapproving.

He unbuttoned his flannel shirt and threw it to the floor, quickly followed by his work pants. I slipped the dress over my head and took my panties off. For the first time in my life, I was nude in front of a man. And not just any man, but a man who wanted to fuck me. Not just any man who wanted to fuck me, either. My father. My father, who was, in no time at all, about to deflower his youngest daughter. My Dad.

My Dad, who was now naked with me. He was solidly built, with a bit of a beer belly that was mostly hiding his erection at this angle. I couldn't decide if that was a good thing or not. His body was hairy, but he wasn't a woolly mammoth. He wasn't fat, but he wasn't in great shape... put it this way, his tits were bigger than mine, but that's not exactly a challenge. He still had all his hair, but it was pretty much all silver now. Clean-shaven always. I watched his hazel eyes explore the sight of me.

He studied my flat chest, my skinny arms, my flat stomach, my neatly trimmed bush, my smooth legs. We were both lucky it was summer and I wear dresses so often, otherwise I'd probably never shave without reason. I started to feel self-conscious, so I moved to close my legs and cover my tits.

That got a reaction. Dad stepped forward again and parted my legs, and pulled my arm from my chest. I let him - this thing was all about teaching me confidence, so I needed to get used to being naked. And letting people see me naked...even if they were my father.

He placed my hands by my sides and positioned himself between my legs. He ran his calloused hands over my bare skin. He played with my nipples, softly pinching them. Surprisingly, I started to relax under his touch. I reached up and started exploring his body, feeling his warm skin under my hands, his rough body hair. I pulled him closer. I wrapped my skinny legs around his large body. He pulled away and reached down. It was about to happen.

I looked down between my legs and saw it properly for the first time in my life. My Dad's cock. It was dripping precum from its thick, purple head. It was hard to tell how long it was from this angle. He shifted his gaze from our genitals to my face and gave a look that said something like "You sure?" or "Ready?"

I nodded.

He rubbed the head of his thick dick against my wet, virgin pussy. We both groaned with anticipation, pleasure and anxiety.

Once he was lubricated with my juices, he lined himself up with my opening. I bit my lip and tensed my whole body with nervous anticipation.

It wasn't as though I'd never explored myself. And thanks to discreet shipping, I had a reasonable collection of dildos and vibrators that ensured there was no trace of a hymen left. But this was the first real, actual dick that was going to be inside me. So of course I was nervous. What would it feel like? Was it still going to hurt? What if I did something wrong?

And, just like that, he was inside me. His warmth, his hardness, his manhood. My Dad. His cock. My pussy. My virginity was officially gone. I took a sharp breath of air, like a gasp. And then I was having sex. I didn't even care it was with my father. He felt so good inside me, against me, breathing on me. His smell, still sweaty from work. I gave myself to him entirely at that moment. I looked him deep in the eyes and moaned.

He started sliding out, then back in. Slowly at first, until he felt me moving my hips in time with him. He sped up his thrusts, so I did too. This was it - we were fucking. We were breathing hard, and I was moaning.

I still had my glasses on, so when I looked down, I could see my pussy lips swallowing his thick cock effortlessly. I watched his thickness spreading me. I felt it sliding in and out of my body. Jesus, it felt so fucking good. Just as good as I'd imagined.

I looked up at him, my father - my fucking father. The man who raised me, the man who freaked the fuck out when Charlotte started dating. Now balls deep inside his youngest daughter. And loving it. He wasn't smiling, but he looked so fucking proud. Of me, or himself, it wasn't clear.

A minute or so later, we were fucking hard. This morning's dishes rattled rhythmically in the sink. The kitchen cabinet doors under me banged in time with Dad's thrusts.

Fucking my Dad in the kitchen on a Wednesday afternoon. Was this how I'd hoped to lose my virginity? Of course not. But was it what I needed at that time? Without a doubt, yes. I pulled him close and fucked back as well as I could, for my first time. Feeling the rhythms of our bodies. I pressed my face against his warm, soft body.

We stayed that way for a couple more minutes, until Dad progressed from panting to grunting. His body started tensing up. I'd seen enough porn and read enough erotica to know what was coming next. I leaned back so I could watch. He pounded my pussy as hard and fast as he could. Watching and feeling and hearing him get closer only turned me on more. I was so horny knowing I was going to make a man cum for the first time.

I didn't have to wait much longer. Dad grunted "Ugh, uuuhhh..." and I watched as his dick throbbed inside me, then exploded. His hot cum gushed into my pussy, filling me up with his seed. His whole body shuddered as he finished thrusting into me. "Fuuuuuck!" he moaned, still breathless.

I was speechless, breathless, and overwhelmed. I was no longer a virgin. I'd officially had sex....With my Dad. "Oh god, oh fuck!"

"Oh shit," Dad sighed. "Are...are you okay, Em?"

"You and me..." I whispered. "That was... We fucked?"

He nodded. He looked worried. "Is- was that okay?"

I wrapped my arms around him and tightened my legs around his torso. I kissed him hard on the lips. Kind of backwards, I know. But none of this was normal. He gave in to the kiss, opening his mouth to match mine. He hugged me back. When the kiss was over, I looked into his eyes and thanked him. "That was...better than I ever imagined, Dad."

"You felt so good, baby. You did good." He kissed my forehead.

And in an instant, the reality of our actions hit me. "Fuck! What about Mom?"

He smiled. "It's okay, sweetie." He paused, thinking, debating whether to say the next part or not. He did. "This was actually her idea, believe it or not. But don't worry about that for now...we need to cleaned up," he instructed. His dick was softening inside me. As he shifted, he fell out and I started leaking his cum onto the benchtop.

"Oh fuck! Too late, I think..." I watched, fascinated, as his cum oozed from my opening. "Oh wow, it's so gross!" I giggled.

Dad, meanwhile, had gotten the paper towels and handed one to me. "Here." He wiped himself and started on the puddle beneath me. "You're...still on the pill, right?"