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Omegle Blackmail - Part 1

Categories Fiction, Blackmail, Coercion, Domination/submission

Author: Berko

Published: 25 January 2018

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*Please note: This is a work of fiction. This story is not real and any attempt to recreate it in real life makes you a terrible human being. I do not condone this behaviour, the fantasy just gets me excited.

More chapters coming soon!

Part 1: The Beginning

I guess I should tell you a little bit of a background before I get into my story. I was always a shy kid growing up. Kept to myself, didn’t have a lot of friends. I spent a lot of time playing computer games online. I guess you could say I was a tomboy. The one friend I did have was my neighbor Scott. We grew up together and most nights would end up playing catch or basketball on the street in front of our houses. My parents were probably worried about me since I didn’t socialize a lot but I was a decent student and didn’t cause any trouble in school so they left me alone for the most part.

I wasn’t a trouble maker mainly because I was so anti confrontational. I hated getting into arguments with people. Whenever conflict would find me, I’d usually just give in so the other person was happy. Looking back on it now, I can see that’s the start of me being submissive but at the time I obviously didn’t know that.

Things started to change in my life when I started reaching puberty. It was the summer before high school started and I remember my body changing rapidly over the course of a few months, conveniently right before school started (or I guess unconveniently, depending on how you look at it). My hips widened, I started growing boobs and my ass became rounder. I didn’t have huge boobs by then, maybe C’s but they looked huge on my tiny body. I guess I had kept a slim physique from horsing around so much that I didn’t really gain any weight, just in my tits and ass.

One day that summer, Scott and I were playing hide and go-seek with a few other kids from the neighbourhood. It was summer time and all of us had nothing to do with our days. We had been to day camp the previous summer but our parents gave up on that after we complained how rigid it was. So they let us stay home and do nothing for the most part.

The group of kids, there was 6 of us, gathered around in the circle at the end of my dead end street and decided that one of the other girls would be the seeker. After she turned around and closed her eyes, Scott grabbed me and we took off running towards the ravine at the end of our street. We got to the entrance and ran up the side of a hill on our left.

“C’mon, let’s get to our usual hide out spot” Scott whispered as we reached the top of the hill.

“Alright, sounds good. But no one could find us there last time, so let’s make sure we don’t lose track of time again” I said, grinning to him as we took off through the forest.

We got to a small hill that had a drop-off behind it and sat down with our backs against the earth wall.

“Let’s give it 10 minutes or so and if they can’t find us, we’ll move closer to check out what’s going on” I said, turning to Scott in a low voice.

He nodded.

We spent some time in silence, listening around for the rustling of leaves to indicate someone was coming up on us.

No one came.

“Hey, can I ask you a question?” Scott said in a whisper

“Shhhh, they’re going to hear us” I said

“No they’re not, they’ll never find us here” he replied “C’mon, it’s just a quick question”

“Alright, sure what’s up?” I said, resigning myself to answering Scott’s stupid question I was sure.

“Well…I don’t really know how to put this…” He stammered

“C’mon already, now I’m curious!”

“Well…I was wondering…what it’s like to have boobs now that you have them.” He stammered

My face went red.

“What are you talking about” I whispered back to him

“You know…what’s it like to have boobs. Does it feel weird having them hang around and be big and stuff?” He said while his eyes dropped down to my chest.

“It’s fine, I guess. I don’t really notice it” I said, surprising myself because I didn’t really feel comfortable talking about my boobs.

“Really? I feel like they’d be in your way all the time”, he replied

I moved my hands up to cover my boobs a bit, silently bitter about wearing a tank top with a sports bra underneath.

“Well does it feel weird to have your penis flopping around everywhere?” I asked Scott. I had only learned about sex-ed in school so I didn’t know much, although I had a general understanding of how boys were different than girls.

“No, I guess not.” He replied

“Well, then, it’s the same thing then. Do we really need to be talking about my boobs?” I seethed at him, turning even more red in the face.

“I guess not.” Scott said and then paused.

I could tell he wanted to say something else but for a couple of moments, we just sat there in silence.

“I don’t think they’re going to find us here.” I said after a few awkward minutes.

“Can you show them to me?” Scott blurted out

“Show what? My boobs? Are you crazy?” I said to Scott

“Yeah, c’mon! I’ve never seen boobs before and we’ve been best friends forever, right? Just show them to me quickly.” He said, licking his lips in a weird way that I hadn’t ever seen before.

I really didn’t want to. At least I don’t think I wanted to. But I also didn’t want to argue with Scott. What’s the harm in showing my boobs to Scott. He won’t tell anyone…

“C’mon…pleassseee!” Scott pleaded, giving me puppy eyes

“Alright, fine! But just for 3 seconds.” I said. I slowly lifted up my shirt, looking around to make sure no one was coming. My hands passed my flat stomach and got to my bra. I looked over at Scott and his eyes were glued to my hands and my chest.

I took a deep breath and hooked my fingers under my bra and my shirt and pulled them both up to my neck. I closed my eyes, blushing like crazy I’m sure.

I think it was 3 seconds later but who knows since time seemed to stop. I quickly opened my eyes and looked at Scott. He was staring at my tits with his mouth wide open. I started to feel something I had never felt before. I got a really warm feeling in my stomach and I started to get slippery down there. I looked over at Scott and then down to my tits. It started getting stronger, I could feel a deep wetness in my panties and a strong desire to stick my hand down my pants.

I had never really played with myself before but I had heard some girls at school talking about fingering themselves. I just kind of assumed you stuck a finger in your hole and it would feel good. But this was something completely new. A strong urge had overtaken me and I could feel my head get cloudy.

It must have been 15 or 20 seconds by now. I quickly shook out of my trance and dropped my shirt and bra over my chest. I looked at Scott.

“There, are you happy now?” I said, still blushing furiously.

“Ummmm…” Scott mumbled

“What?! I couldn’t hear you.” I said

“Yeah. Um. I’m happy. That was amazing Heather. You have amazing tits. They’re perfect. Not that I’ve seen any before. Well online but that doesn’t count. That was awesome.” He explained. He moved his feet around so he was sitting cross legged. I thought I saw a bulge in his pants where his penis was but I wasn’t sure.

“Good. Well thanks I guess? Don’t get used to it, it’s not going to happen again.” I said, more trying to convince myself than anything. That feeling I had got when Scott looked at my tits was exhilarating. Just the realization that showing my body off to someone had clearly turned them on was intoxicating. My panties were absolutely soaked.

“I should go home.” I said, quickly standing up, not waiting for a reply and taking off running home.

I got to the side door, quickly opened up and bounded upstairs to my shower. I stripped completely naked and turned to look in the mirror, taking a deep breath. I guess my body was pretty good. I had a flat stomach, big-ish boobs and an athletic ass with a bit of cushion/definition to it. I guess I was a pretty hot girl even though I would’ve never considered myself to be one of those girls.

I ran my hands over my boobs, my nipples were rock hard and pointing out about an inch. My hands slowly travelled lower to my vagina and I ran my hands through the soft fur that had grown there recently. There wasn’t much of it, but it was getting a bit curly.

My hand found my opening and it was sopping wet. I slipped my finger inside and in the process, hit the top part of my vagina and I got a jolt of pleasure. My finger moved tentatively towards that little button that caused it. I circled it slowly, feeling an intense wave of ecstasy wash over me. I continued rubbing and rubbing and rubbing until I couldn’t handle it anymore, then I stopped. I wasn’t really sure if I had done it right but it had felt amazing. I got into the shower and rinsed off, thinking more about how good it had felt to show my tits to Scott.

Part 2:

A couple years passed and Scott and I never spoke about the incident in the trees that one day. We were still best friends and did everything together. I think our parents thought we were going to get married but I was still a tom boy in a hot girls developing body. All I wanted to do was run around and play video games.

One day while I was screwing around on YouTube, mindlessly watching random animal videos while I was bored on a Saturday, I noticed an ad for a website called “Omegle”. It said, “Chat with strangers around the world. Try Omegle. It’s free!”

I figured, why not? I don’t have anything better to do. So I decided to click on it. I landed on the site and it seemed pretty straightforward. It asked if I had a webcam, which I did on my laptop, so I clicked in to the start button. The button twirled around for a bit and then I got connected to my first stranger.

For a second, all I saw was a black screen. And then a strange object popped into the screen. I wasn’t really sure what it was. Until it moved back and I saw it was an erect penis attached to a random man! I shrieked, good thing my parents weren’t home, and slammed my laptop shut. I was freaking out and taking deep breaths. I had never seen a penis before, never mind an erect one. I had never visited porn sites on the web or had seen one in person. I had a general idea of what one looked like but never thought it could change into that.

I looked around my room, half expecting someone to pop out of somewhere and make fun of me. I was blushing. I turned around from my desk and lied down on my bed, grabbing a book in the process. Enough of that site, I thought to myself.

I started to read. 10 seconds in my mind started to wander. That penis was interesting. I had no idea they could look like that. I wondered what sort of website would have a random guy showing his dick to strangers? That must have just been a bad apple. I couldn’t believe it but I could feel my pussy start to get wet (I had learned the word pussy from a friend over the past little bit). How is that possible, I thought?

Well seeing an erect penis might make me horny, I gathered. Let’s go back to the site and see if there’s other normal people who really just want to chat. I gathered myself, got back up and sat down at my desk, opening my computer.

Omegle reloaded and I was back at the home screen. I pressed “begin” and it started twirling again. The first video feed that popped up was a guy’s face. He smiled at me.

“Oh, this is better.” I said to no one in particular.

I smiled back and waved. I saw him grabbing his webcam and pointing it down towards his crotch. His erect penis was hanging out of his pants. I gasped and immediately clicked “next stranger”. Another penis on the screen. I tried again. Another guy holding his dick. Is this entire website filled with guy’s showing their dicks off, I asked out loud.

Then my eyes fell towards the screen. And I noticed how cool it was. I mean, when I really looked at it, it was neat. Hard and veiny and it was dripping some sort of fluid from it’s tip. I started to feel myself getting more turned on.

I started typing.


Hey, what’s up? He replied

N2m, hbu? I said, trying to be normal even though this guys dick was staring me in the face kind of.

Same, just chilling. Do you want to have some fun? He said, taking his hand and stroking his dick upwards once and another drop of liquid appeared from the tip.

What kind of fun? I said

Do you like to watch guys jerk off?

I don’t know, I’ve never seen it before

Well how about I show He said, grabbing his dick and stroking it steadily now. Going up and down. I stared at my camera, mesmerized. It was amazing. I could feel myself getting soaking wet now and my hand creeped to my pants subconsciously.

Yeah, that’s it, play with yourself too He typed

I snaked my hand down my sweatpants and onto my slippery pussy, running my finger up from the opening and taking juices to my clit. I rubbed all around it, sending shivers through me. This was sensory overload and my body could barely handle it. Almost immediately I started to orgasm. In the past couple of years, I had become a lot more comfortable with my body and had explored every inch of it. Now, I was a master at getting myself off. But I had never cum so quickly before in my entire life.

Whoa, did you just cum? He typed

Ummm. Maybe, kind of. I replied

That’s so hot. Do it again.

I looked at his words. I didn’t really feel like doing it again but there was something about how he said it that really started to turn me on again after my orgasmic high. It was a demanding tone, like he almost expected me to do what he asked for. I looked at him stroking his dick again even though I thought I had gone far enough for one day, I embarrassingly admit that I didn’t turn it off.

I moved my hand back down to my pants, slipping it under my panties and onto my pussy once again.

He started stroking faster.

That’s it. Keep going baby.

I continued rubbing all around my opening, going slower this time around. I couldn’t take my eyes off his dick. It was so wet and shiny now. It must have been the liquid I saw earlier. I wonder how that works, I thought to myself.

Why don’t you help me out a bit? He typed.

What do you mean? I replied

I dunno. Take your shirt and bra off. He demanded

Again, I looked at the words on the screen and got instantly more aroused. I had a feeling in the back that this was a bad idea. But my mind was hazy and it didn’t really feel like I was in control.

I nodded to the camera. I took my hand out of my sweatpants and brought it to the hem of my shirt. I began slowly lifting it up. My face started to get red. I was embarrassed but also more turned on than I had ever been in my entire life. It felt like my entire panties were soaked like I had peed in them. My hands slowly crept up to my bra and I hooked my fingers under it and lifted them both over my head quickly. Like I was hoping to get it over with quickly.

My boobs sprang free and bounced around while I worked to get my shirt and bra off. I got them off finally and brought my hands to cover my tits, even though I’m sure they were just on display for a bit.

Holy crap. Those are amazing. Move your hands. Let me see them. He typed

I dropped my hands, my face going the darkest shade of red possible I’m sure.

Wow. Those might be the best pair of tits on a girl ever. And I’ve seen my fair share. He wrote

I felt a little weird when he said that. Almost like pride that my body was so hot. It felt good to show this stranger my perfect boobs. Even though I was never really interested in guys before, this was different. I was the one who never got attention at school from boys, or heck, even from the other girls. This random stranger online was talking to me. And he liked me. Well, the way I looked. Either way, it was a serious confidence booster. I felt myself getting wetter.

As if on queue, he wrote;

Keep playing with yourself baby, I didn’t tell you to stop.

I slid my hand down into my pants, continuing to watch his throbbing dick on the screen. He started speeding up. Quicker and quicker and quicker until all of a sudden, a giant white liquid spurt from the end of it. I was shocked. I had heard a bit about how babies were made and the role sperm played but I had never realized it was so forceful. It was amazing. I couldn’t take my eyes away as spurt after spurt of white stuff came out of this stranger’s dick.

Finally it was over and he typed.

Cum for me one last time before I have to go.

I quickened my pace but it didn’t take long after witnessing that magnificent display on my screen. I quickly felt it building inside of me until I couldn’t take it anymore. I closed my eyes, gritted my teeth, and had the biggest orgasm of my young life. I took a deep breath and opened my eyes. The stranger was gone. My screen was back on the home screen. I closed my laptop and got into bed for a nap, exhausted both mentally and physically.

Part 3:

I woke up a few hours later, opened my phone in bed and saw an email come through. It was from an address I had never seen before. I opened it.

“Hello Heather,

You don’t know me yet but we’re going to become good friends. Add my Skype ID (Jaxxxter) if you know what’s good for you. And if you don’t, just see the attached screenshot from our little ‘session’ earlier. Be online at midnight tonight.



My heart dropped into my stomach. I slowly moved my cursor over to the attachment but I could already feel that this was going to be something terrible. I clicked on the file and an image opened of me at my desk, topless, with my hand down my pants, clearing in the middle of the throes of an orgasm. My mouth went dry. What did this guy want? I was in so much trouble, I thought to myself.

Continued in Chapter 2!

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Omegle Blackmail - Part 1

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Comments (1)
lamo66 — 26 January 2018 04:49
Yes chapter. 2
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