Omegle at the Sleepover - Part 1

Everyone is 18. This is fiction.

Young, boyish, curly hair, great abs, bubble butt, hairless downstairs front and back. White skin, jet black hair, smiles a lot.

That’s what I wrote in the Omegle chat to describe my friend, who was being shy and was waiting off screen. Bradley was over tonight for a sleepover. The girl on the screen had promised to show us her tits, but then she started being coy, so I was trying to get her to move forward. She said she wanted more. I was getting frustrated seeing her big titties caged in her tight shirt, when she finally dropped the big one: she asked us to take out our dicks and jerk each other off. 

I dropped my mouth in shock, having never done anything like that before. Even at parties when people started to hook up, I never really saw a dude’s dick, just saw that he was getting a blowjob or that he was fucking someone. I had to admit I liked when my friends got naked around me, for whatever reason.

Bradley had a different reaction than me, and he immediately took out his hard dick and rolled his chair over so he was on screen. He stared at the girl on screen, and held his cock from the base sticking it straight up. I was shocked a second time because he had a fucking monster cock. This thing was veiny and simply large, both girthy and long. I couldn’t believe he was ever shy around the ladies. I stared at it and said “What the fuck dude?”. He didn’t answer, just stared at the girl on screen wagged his dick around from the base.

It was thick and tall, and it actually stood out against the rest of him. It literally seemed like a different looking third leg. It was at full mast already with a line of clear precum running down the side. He started rubbing it out of instinct, eyes fixed on the girl on the screen, then slyly glanced sideways at the bulge in my pants. I unzipped my jeans and pulled them with my underwear down to my ankles. I was about half hard.

“I’m too nervous to get hard” I said to him, while keeping my eyes on the screen. He chuckled.

The girl finally took her top off completely, and she pulled her shoulders back, displaying her perky B/C cups. Both our eyes were fixed on the screen, with our hands on our dicks. She said “Ok, now jerk off your friend”.

I surprised myself with how little I hesitated, and I grabbed his dick, pushing his hand away. He just lifted his hands into the air awkwardly and started giggling uncontrollably. It kind of just felt like holding his hand or his wrist to me, except slightly wet from his precum. It didn’t make me feel as uncomfortable as I thought it would. I noted in my head how big it was, and how I couldn’t get my hand all the way around it. It was so different than mine, even though I was pretty sure mine was pretty big, since it usually matched the average you see in porn. And, his cock was actually much harder than mine. Like it felt like a literal piece of wood wrapped in skin, with just a layer of flesh around it. Mine didn’t get that hard at its peak, like 80% of that hardness maybe. I could feel his heartbeat, like I was connected deep inside his body through his cock.

I couldn’t help but smile at the silliness of this whole situation. And I admitted to myself that the taboo nature of this was turning me on in a novel way, but I thought it was still because of the tits on the screen rather than my friend’s big cock in my hand. I could tell at that point that this was something we were going to talk about later that night before we went to bed.

The girl on the screen said “Why aren’t you touching him?” referring to Bradley. 

He just said “I don’t know” with a huge goofy smile still on his face. 

“Would you suck him?” she said nonchalantly, with sort of a wink to her facial expression.

Bradley glared suspiciously at her, “Why?” he said, with an implied lmao that’s weird.

My dick did a little twitch and began to rise closer to its potential, and I started playing with it with my left hand, while gripping Bradley’s with my right, although I’d stopped jerking him off for the moment, a little shocked at the suggestion she gave.

“I don’t know, I’m bored I just wanted to see if you’d do it.” She said.

“We’re not gay” Bradley said, “sorry”. 

That was the expected response from Bradley, and me too to be honest. I don’t know where this came from, but I piped up “I wouldn’t care if you did”, adding in “no homo”.

Bradley stared at me, and it seemed like he was thinking about it. And, although I didn’t expect him to go further into this at all, he absolutely shocked me by saying to the girl “What will you do for us?”

I dripped out some precum at the suggestion that he was up for sucking me. Inside I was electrified, I could feel it in my fucking nipples.

She hesitated, and said “Umm... I’ll show you my pussy.”

“Deal” I said, honestly more excited about the blowjob than seeing the girl at this point.

“Alright you first” Bradley said. His dick was still at full mast, and throbbing a bit, and I let go of it, wiping his precum off onto his thigh.

The girl sighed, and moved her laptop screen down so the camera angled toward her pussy, and she lifted her shirt, showing a tight tummy and pink and white striped panties. She lowered the panties to show a smooth pussy. It was hot. My jaw dropped and I stared, then looked at Bradley. He had grabbed his own cock and was lightly tugging at it. She kept the camera on her pussy and started rubbing it with her fingers in circles. She let out the lightest moan, then said “your turn”.

I got pretty excited at this point, but Bradley wasn’t “going down” that easy lol. He tried a delay tactic “I never actually agreed to it”. She chuckled, but said “if you don’t I’m just gonna hit next and find someone who will”. 

“Dude I know it’s gross but how often do we find a live girl that’s actually decently hot, and also willing to show us her pussy.” I suggested, adding “We just showered together after swim practice so you know it’s clean and not sweaty or anything.”  I was angling for my cock to get the attention it deserved. Plus, having Bradley suck my cock would make me feel somewhat superior after my ego had taken such a hit having to see how big his hard dick was. I’d seen it soft all these years in swim team showers, so I knew it was big, but I had no idea it was like BIG big, even after hearing the slutty girls gossip about his giant dick around school.

He rolled his eyes, gave a heavy sigh and looked anxious. “Fine but when we tell this story we leave this part out.” My heart skipped a beat and my stomach turned upside down with butterflies. I literally bounced my bare ass in the chair a bit out of excitement, but also in an effort to slide down and make my dick more reachable for Bradley.

He got down on his knees in front of my chair, his pants still at his ankles. From this angle his ass looked just like a hot girl’s, and I was excited to be honest. He gave one last glance back at the girl’s live pussy on the screen, then turned to me and just licked the shaft a little bit. 

“Nice” said the girl, and began rubbing her pussy more vigorously.

Bradley began to bob his head on my dick and I rapidly grew to full mast inside his mouth. Beyond the initial shock of sucking a dick which I’m sure he felt, he seemed to get the hang of it quickly, although he kept gagging on it multiple times. 

After about five minutes I thought for sure he was gonna give up, but he just took a break, kept his hand on my dick, turned to the screen and asked “How much longer do I have to go?” 

“Until he finishes” is all she said.

He rolled his eyes and went back to work on my cock, this time with gusto. He used his hands at the same time as his wet lips and pumped my cock tightly from bottom to top, taking breaks only when he gagged. Around this time the girl suddenly disappeared, and the “chat ended” screen popped up. I was disappointed for a second, but then I realized I didn’t have to tell Bradley. I let him continue because it simply felt too good. When I was about to cum I almost pushed him away but then thought fuck it and let it spray away inside his mouth, assuming he’d be pissed but he would forgive after. To my surprise, he just froze and started to gulp it down as it came out. I was shocked and thrilled at the same time—this was kind of the best feeling of my life. A bit of cum escaped and rolled down to my balls, and he instinctively reached down with his hand to wipe it up for me. He turned back to the screen to find the girl had disappeared. He wiped his hand on my abs and my underwear. 

“What the fuck, why didn’t you tell me she left?”

“I wanted you to finish” I admitted, with a slightly apologetic face, and my cock still hanging out, resting on my thigh.

“You own me one, you dick” he responded. 

“Dude it kinda seems like you enjoyed it to be honest” I said, pointing at his protruding naked erection. 

“Oh you think so?” He responded, still pretending to be offended.

“Honestly dude, I do owe you one and you’re an awesome friend. Would you want me to finish you off in return? ”

“Are you serious? There’s not even a girl asking us to do it—that’s kinda gay!” He exclaimed, half jokingly, but one corner of his mouth curled upward. I wanted to say You’re the one who just turned yourself into a girl for me but I didn’t. 

Instead I said “what was that like? You honestly seemed to be having fun.”

“You’re about to find out,” he said as he sat in the chair and held his massive pole up for me and smirked, “no homo.”