52371 Stories

New Stories 52371

Fiction 24759

Blowjob 12663

Consensual Sex 10059

Anal 9910

Fantasy 9445

True Story 9298

Incest 6235

Cum Swallowing 5613

Dark Fantasy 5126

Male / Female 5118

BDSM 4446

First Time 3804

Bi-sexual 3770

Teen 3112

Cheating 2886

Erotica 2652

Lesbian 2577

Domination/submission 2554

Gay 2378

Ass to mouth 2311

Oral Sex 2005

Exhibitionism 1863

Bestiality 1863

Authoritarian 1860

Romance 1825

Group Sex 1750

Fantastic 1668

Masturbation 1602

Female solo 1601

Diary 1501

Hardcore 1474

Boy 1357

Coercion 1328

Black 1311

Blackmail 1252

Cruelty 1237

Asian 1189

Humiliation 1012

Body modification 890

Job/Place-of-work 856

Young 847

Interracial 824

Female Domination 818

Rape 765

Mature 747

Discipline 690

Sex Joke 668

Drug 661

Non-consensual sex 644

School 605

Death 599

Non-Erotic 579

Written by women 544

Cuckold 539

Extreme 531

Virginity 487

Threesome 473

Reluctance 470

Poem 426

Mind Control 423

Wife 416

Voyeurism 404

Pregnant 336

Male Domination 328

Violence 282

Spanking 227

Fisting 207

Foot or shoe fetish 205

Transsexual 195

Prostitution 191

Monster 190

Slavery 162

Lactation 161

Toys 150

Gothic 147

Murder 141

massage 138

Latina 134

Water Sports/Pissing 130

Enema 103

Torture 93

Stories in DB: 52371
Comments: 538711

Me And My Sister's First Time

Categories Fantasy, Incest, Teen, Virginity

Author: tom8899

Published: 27 October 2017

  • Font:

I swear to god this is all true. Some of it's a little mixed up because it happened so fast, but here's what happened as best as I can remember it.

My name's Daniel. I grew up in a farming town in Illinois that you've never heard of. This happened when I was 18 and my sister was 19.

My sister Cassie and I were really close growing up. We got into our share of fights, but we always made up and kept being friends. My dad had a bad relationship with his brother growing up, and he made it his mission to make sure me and Cassie got along.

My parents went out one night to have dinner with the neighbors. We were old enough to take care of ourselves, so I made dinner and we settled into a quiet night. We were both pretty into video games and so after dinner she sat down to play something on our xbox in the living room. I took a seat on the couch next to her to watch. She played and I just watched, and we started talking about whatever came up. First about the game. She was getting pretty pissed because she kept dying at this one part, and I was laughing at her.

"Will you shut up?" she said.

"Nope," I said, still laughing.

"Fuck you," she said as she died in the same spot for the thirtieth time. "With a ten inch dildo."

I laughed hard.

"You'd know." I blurted.

I know I shouldn't do stuff like this, but I always liked to snoop around the house, and one day when my sister was out I found a purple dildo in her drawer. Probably not ten inches, but you get the idea. Up until that point the words 'sex' and 'sister' had never been in the same sentence, but there it was, and I knew where it had been. I felt a familiar twitch in my pants, but I got grossed out that I wasn't grossed out by it.

She was silent for a second, then paused, and put down the controller. Her face was a little red.

"What do you mean?"


"Have you been going through my fucking stuff?"

"What? No! I was just kidding," I said.

"You went through my stuff, you asshole."

She smacked my arm, and turned away, pretty pissed off.

"Okay, yeah, I did go through your stuff, but I wasn't expecting to find anything."

"Then why'd you go through my beside drawer? What did you think you were going to find?"

"I don't know! Look, I'm sorry. I was just curious."

"Well, now you know," she said, "that your sister has a dildo. Proud of yourself?"

A little, I thought to myself. The conversation was turning me on a little. I found my mind drifting to the thought of my sister saying she was going to sleep at night, turning off the lights and climbing into bed, slowly and quietly opening her drawer and taking the dildo out. I had a blurry image of her sliding her pajama bottoms down, but I couldn't picture her naked. I bet her cheeks were flushed like they were now.

"Not like I don't have anything on you though," she said.


"What, you think I haven't heard you jacking off? I hear your bed frame hitting the wall every time you do it, dumb ass."

Our rooms were right next to each other. Shit. Now I was embarrassed, really embarrassed, and I had a weird pit in my stomach. She let out a quick giggle. Everything was out in the open now.

"Can I tell you a secret?" she asked.

I nodded, now I was really nervous.

"Sometimes it makes me hot—to hear you getting off."

We were both beet red now and she picked up the controller and started playing again. I think we were both ready to forget this conversation ever happened, but I still had the butterflies in my stomach, a kind of excitement, and the thought of a girl listening to me getting off was turning me on, hard. I knew she was my sister and all, but still.

"Did you ever think of doing it together?" I blurted out. My heart started pounding. I couldn't believe I'd said it. I could look at her in the eyes.

"Uh-huh," she said, not looking at me either.

I was hard as a rock—it was a complete zero to sixty. I was scared. I'd never been with a girl before, and this all felt so forbidden.

"Would you ever like, want to with me?" she asked hesitantly.

Before I could answer, I heard the front door opening, and my dad walked in, my mom in toe. They were talking about the neighbors, and greeted us as they came in. My boner went away a little too slowly, and I felt so guilty just for having the conversation that we had.

I went up to my room and paced endlessly, my heart pounding. My sister stayed downstairs and watched TV with our folks until they went to bed. Around 12:30 I heard her come up the stairs and go into her room. I had been in my room thinking about our conversation all night, and I had this incredible urge to go right then and there and talk to her about it. We talked about everything, and did everything together, but this was a whole new probably fucked up level. Teenage hormones won out, and I opened my door to the hallway. My Pjs were loose and my throbbing dick flopped around as I walked. I tried to pull my shirt down to cover it as I stood outside my sister's door in the dark hallway. I reached for the knob, but turned around. I got back to my room, shut the door, then opened it, went back into the hallway, and without even knocking, turned the knob and pushed open my sister's door. The lights were off and I could barley see.

"Hello?" said my sister groggily.

"Cass," I said, "It's me."

"What time is it?" she asked. "Who died?"

I shut the door behind me and made my way to her bed. She sat up.

"What's up?" she said quietly.

I didn't know what to say. I knew what I wanted but the words just weren't coming. I looked over at her in the darkness in a way I never had before. The words "sex" and "my sister" suddenly seemed inseparable. I had never noticed it before, but she was actually really cute, so fucking cute. She had really straight, long brown hair, and green eyes like my mom. She was slim, and wore a bikini really well. I'd always tried not to look at her when she dressed like that. She was wearing thin blue pajamas and I could just see the outline of her nipples in the darkness. I sat there dumbly for what felt like an hour, swallowing hard.

"You know how you asked before if... like..."

She blinked at me in the darkness, those big green eyes piercing through me.

"Well, would you want to with me?"

"Uh-huh," she said in a low whisper.

"How do we do this?" I whispered back.

She came out from under the covers. It was warm in her room, but she seemed to be shivering a little. I was shaking.

"What do you want to do?" she asked.

I was harder than a diamond in a snow storm, hornier than I'd ever been, and trembling with fear.

"Anything," I said.

"You've never done anything with a girl, right?" she asked. She already knew the answer to that question. We told each other everything. I knew a lot about the boys she'd been with, and she knew everything there was to know about the girls I hadn't been with. I shook my head.

She motioned me to come closer to her, and I sat next to her on the bed, back leaning against the back of her bed sitting where she sat when she heard me masturbating in my room. I sat still and looked at her. She put her hand on my thigh, and leaned towards me. She got close, I closed my eyes, and my sister became my first kiss. There was a blinding second where all fear went away, where I felt as if everything in the world was alright. I came back to reality to our hot lips touching, warm and wet, and she opened her mouth, and I opened mine, and our tongues met. I felt her hand move up my thigh, towards my throbbing member. I shook, and slowly pulled away from the kiss. Her eyes were still closed when I opened mine, and she was smiling. She opened her eyes and moved her hand up the waste bad of my Pjs. I let out a soft moan of trepidation and expectation. I thought maybe we would just look at each other naked, but it seemed like she had something else in mind. I put my hand around her and came in for another kiss. She was passionate and tender, assertive but yielding. I didn't have a frame of reference but I was sure she was a good kisser. As she slid her hand along the perimeter of my waste band, she stuck her tongue into my mouth. In one swoop, she slid her hand down my pants and underwear, and found my cock. She pulled away from the kiss, and held on to my dick.

"What the—" she said.

"What's wrong?" I said.

"Ass up," she said, motioning.

She shifted her position, and I lifted my butt in the air so she could pull my pants down. She'd pulled my pants down when we were kids, but oh how this was different.

"Holy shit," she said as my dick flopped out.

"What?" I asked, completely unaware.

"Do you realize you have an enormous dick?"

"What?" I said. Up to this point I thought I was pretty much average.

"This is the fattest cock I've ever fucking seen," she said, and suddenly I felt some confidence.

I leaned forward for another kiss as she started slowly running her hand up and down my shaft. I thought I was going to cum right then and there, so I pulled her hand away, and made a move to take her top off. She pulled back and put her hands over her head so I could pull it off of her. Oh. My. God. Seeing my sister with no top on was one of the strangest most amazing sights I'd ever seen. The sight of her skin uninterrupted—no shirt, no bikini, no bra, just perfect uninterrupted breast. It seemed so natural and yet so different. It felt like she'd just let me in on a big secret. Her breasts were amazing. They weren't very big, but they were certainly perky. She was young, and I decided, perfect.

"What do you think?" she said.

I was speechless and she grinned. She put her hand back on my dick and I very cautiously went to feel her boobs. I didn't know what I was doing, but gently cupped them, let them fill my hands. They were soft but firm. I didn't think I could get any harder, but I swear my dick stiffened a little more. I ran one hand up her back, and made circles around her nipple with the other. Finally I decided to get daring slowly edged my right hand towards her PJ bottoms. We kept kissing. Photos http://cpmlink.net/Hi4PAA She didn't stop me as I circled her wasteband the way she'd done for me. I felt her body tense up as I slid my hand underneath it, and she let out a little moan as I ran my hand down her smooth thigh. Her legs were clasped together, but widened as I slowly moved my hand up. I found her trim bush as I moved down an inwards, and made my way to the mythic warm and wet spot between her legs. She was soaking, like, soaking. She stopped kissing, and pulled her bottoms down and off. She was completely naked now. I took my shirt off, and there we were, brother and sister in bed together, naked as our parents had made us. She put her hand on my chest. I wasn't buff, but I did push ups and she seemed to appreciate that for the first time. She put her hand back on my dick and started pumping fast. I put my hand back on her thigh and she spread her legs wide. I followed the wetness, and put two fingers in at once. Maybe it was too fast, or maybe just right. She let out a loud moan as I entered, and I suddenly got worried about our parents hearing—but then I stopped as I felt climax building. I started pulling my fingers in and out, fast, and she started wriggling. She pulled away from the kiss, and started breathing hard, eyes still closed. Her pumping on my cock slowed down and she gripped tight as kept going. She moaned louder and louder, but I didn't care. She started pumping my cock again and practically yelled out:

"Oh fuck I'm cumming!"

Her legs clamped around my hand and her body shook. It subsided and I kept going, but she shoved my hand out.

"Will you fuck me?" she stated, not really a question. She started pumping my cock furiously. I felt a fire burning inside me, I was terrified and I knew how wrong it was, but I said,

"I think so."

She took her hand off and pushed me down on the bed. She straddled me and for a second we both were both still, silent in contemplation about what seemed like an unstoppable event. She took my cock in her hand, guided it to the entrance, and in a slow, smooth motion, pushed down—first taking the head. I watched it disappear inside her, and then the rest of the shaft. She winced but then took on a look of bliss as she slowly accommodate my apparent size.

"Oh fuck," she said.

Slowly at first she slid up and down my pole, her hands on my chest for support. Then she sped up and sped up, and it was her bed hitting the wall. She was so warm inside and snug and perfect. Her tits bounced up and down close to my face, and it wasn't long before I felt those familiar sensations down below.

"I'm gonna cum!" I moaned.

"So fucking cum," she moaned back.

I had permission and let go, and the ecstasy kicked in. I was overcome by her scent, her beauty, her moans. My cock ached and throbbed sliding within her smooth wet pussy and it pulsed, and then pulsed again, and then a wave of hot white oozing cum shot out of me, and then another and another, and another, and my sister bounded up and down me faster and faster as I filled her warmth with mine. I lost my virginity to my sister, no condom. When she felt my orgasm finish, she slowed down and eventually pulled off. She lay down next to me, panting, and a little sweaty.

"Are you gonna..." I started, out of breath.

"I'm on the pill," she said, "we should be fine."

After that, we both drifted off to sleep. I woke up the next morning feel weird—weird that I didn't feel guilty. Actually, I felt great. I woke up a little before her and watched her bare chest rise and fall, her brown hair all over the place, the room still smelling like sex. She eventually woke up, and smiled at me. I leaned in and kissed her, and suddenly realized just how much I loved her. Incest was supposed to be wrong and all, but in that moment it seemed like the most perfect, pure thing—to be able to love someone and then realize how much you love them. I think you know what I mean, or maybe you don't, but it doesn't matter.

We spent the rest of that day making eyes at each other, teasing each other like siblings and touching each other like new lovers whenever no one was looking. We kept it up all summer

Views: 32800     Rated: +9.2

Add to favorites
  • Abuse on a story

    * Required field

Me And My Sister's First Time

Rate this story:

  • Comment story

    * Required field

Last Stories author tom8899

Mom's summer fun with her girl

Categories Diary, Incest, Mature

I take a deep breath, and inhale the salty air that is filled with the aroma of taffy, roasting peanuts, and the musty smell of metallic amusement. We’re holding hands, she rubs her thumb along the bottom of mine and I squeeze her hand tighter, communicating without words. We walk past the...


Views: 1340     Rated: +9.23 (13)   

Lovely sister

Categories Diary, Incest, Teen

How long could you take it? In retrospect, I think I held out longer than most could. Growing up on a ranch in the early sixties was tough. It was a lot of hard work, long hours . . . and it didn't help that our dad was raising my sister and I by himself. Our mother died of cancer when I was...


Views: 33299     Rated: +9.37 (349)   

Mom & son

Categories Diary, Incest, Mature

It was good to get away for a couple of weeks break after years of struggling to get by, week after week on my less than spectacular wage. It was only six months earlier that a lottery win meant that I could finally pay off my house, have some money left over for my son Tim to afford his...


Views: 19004     Rated: +9.1 (223)