Cherry Popped Pt. 01

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A chance encounter at a bar, a night to remember.
1.1k words
4.25
15.8k
19

Part 1 of the 2 part series

Updated 06/15/2023
Created 04/30/2021
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19 Followers

Maybe it was over laundry. Or chores. Whatever it was, my girlfriend got mad at me, and off I went to the pub. That's how I met Rob. This tall blond stranger sat down next to me and started a conversation. His intentions were obvious, and bi-curious me was flattered by the attention.

We talked about my girlfriend, his childhood, and with more booze, the conversation quickly turned sexual.

"You look like someone who enjoys being with girls and guys," he half-yelled over the pub noise.

"How so?" I said, feigning surprise. "I've never even been with a guy."

Two seconds later, Rob put his hand on mine, looked into my eyes and said, "You know, there's a bunch of us boys and girls at my place having fun. Maybe, join us?"

My heart skipped a beat at his touch, but I soon found myself in the back seat of a cab, going back to his place.

At His Place

Unsurprisingly, there were no boys and girls. It was a bait I didn't mind taking. Rob took a quick shower, and appeared in a terry cloth robe. He handed me a towel, but I was too nervous to even look at him. With the booze wearing off, I took deep long breaths in the warm shower, trying to calm my nerves. What am I doing? I'm going to bed with a strange man, at his apartment. Finishing the shower, I wore the towel and stepped out into the bedroom, chilled by the 11pm winter. And there he was, sitting on the bed, already naked, waiting, and erect.

With barely any eye contact, I walked the two meters separating us, and started kissing down his neck and chest. I took a nipple into my mouth, and gave it a little bite. He sighed his approval. Despite my obvious arousal, I wasn't even hard. I felt awkward and confused. What is happening here? Is he going to fuck me? Should I fuck him?

Rob sensed my unease, and rolled me over onto my back, discarding the towel. He started kissing my mouth, and the sensation of having a stubble against my face was ticklish. I started to laugh, and my nerves eased. I dared myself to open my eyes, and met his gaze. His beautiful, grey eyes. There was no longer any doubt about roles. He owned me, and I was going to be his bitch. Slowly, his kisses made their way down my body, and I was beginning to relax. He was making his way down from my belly button, and... stopped. A long sigh escaped my mouth.

Getting up on his knees, he made his way towards the head of the bed straddling my body, his manhood staring me in the face. For the first time, I noticed his uncut penis. It was not thicker than mine, but a good few centimeters longer. I took it in my hand, and tentatively kissed the head. There is no going back. Opening my mouth, I slowly took the head in, savoring the taste and smell of my first cock. Emulating my girlfriend, I pulled the foreskin back with my lips, then started licking the bottom of the head. From the way he threw his head back, I knew I was doing a good job. I stuck my tongue out, trying to catch his balls, but they were completely out of reach.

"You're such a natural cocksucker," he said, pulling himself out of my mouth. Dragging me by my shoulders, Rob repositioned me so my head was hanging off the edge of the bed. Getting off the bed, he stood just above my head, and pinned my arms to the bed with his hands. Knowing my place, I opened my mouth and received his cock.

Gently, he pushed it all the way in, and bumped against the back of my mouth. As he pulled out, I tried adjusting my head to straighten out my throat. And on his fourth gentle push, I was rewarded with balls slapping on my eyelids.

Rob grunted his approval of my deepthroating him.

I belatedly realized that having my arms pinned to the bed meant I couldn't control his depth, as he started humping my face in earnest.

Gasping for air and fighting my gag reflex, my crotch was begging for stimulation. I pointed to my cock with my right hand.

"Unnffff," I said, face full of balls, expecting to have my arms freed. Rob pulled out, saliva trailing his dick and running down my face. His upside-down face appeared.

"No, later. I have something special for you."

He moved me back to the head of the bed, took his place on top of me, and spread my knees back to my sides. He kissed my saliva-and-precum slicked forehead with a surprising tenderness.

"Do you trust me?" I smiled and nodded yes. In a show of submission, I held the back of my knees with my hands, keeping them spread. He stepped back to fetch lube from the drawer, his eyes never leaving the prize I was presenting to him. I felt myself blush at the attention.

Duly lubricated, his two fingers immediately found my prostate, sending me to heaven. "Ohhh, thank you, ahhh," I moaned, rolling my eyes. Soon, a pool of precum started to form on my stomach. I felt as if he had his fingers massaging my dick from the inside . All I wanted was to have this beautiful stranger fingerfuck me forever. But suddenly, forever stopped. I lusted. I sighed, "please..."

"Please what?" Rob asked, pulling his fingers out. Good question. Fingerbang me some more? Deepthroat me? Let me jack off? He chuckled a bit, then I felt the head of his dick on my ass. I pulled my knees higher, inviting him in.

He made his entry surprisingly gently. Maybe he wanted to go easy on a virgin. But I wasn't one. I loved being pegged, and collected dildos for my girlfriend to use on me. I'm not a butt virgin, and I wanted him to know. I dug my heels into his ass, urging him on. His elbows found the back of my knees, replacing my hands. I was completely spread out, his weight bearing down on me with every thrust. I was being a total butt slut, and loving it.

"I want to come with your dick in my ass," words I didn't know I had in me.

My dick was pointing straight at my face, asking for sweet release.

"No, later," he grunted. Later when? My prostate was sending intense pleasure waves to my brain. I didn't want him to stop, but he suddenly pulled out and jizzed onto my stomach. I was hoping he would cum inside, and was disappointed that he didn't.

With one last shot, his body fell on top of mine, his cum slicking where our skins meet. He kissed me again, and I still wasn't used to having a stubble against my face.

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4 Comments
AnonymousAnonymousalmost 2 years ago

Nice short story. Where I lived it was difficult to find a man to have sex with, so you go with what's available.

Thus my cherry was popped by an older, sweaty bald guy I worked with at a factory, it was very rough but I liked it and he was very happy to work my ass.

clingwrapclingwrapalmost 3 years agoAuthor

@sp9983

Yeah, I originally thought the story was too long, so I split it into two halves. Have received another comment that it was now too short, haha.

Would appreciate comments at the end of pt2, as well

https://literotica.com/s/cherry-popped-pt-02

sp9983sp9983almost 3 years ago

Could have been longer.

AnonymousAnonymousalmost 3 years ago

This story ended very abruptly and thus seems incomplete. What’s coming later? Rob seemed hesitant to suck him or let him cum. What’s up with that. There was an odd feeling that something (good or bad is not clear) was getting ready to happen. Please continue with another chapter!

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