Cucking My Boyfriend for the First Time

"My boyfriend made a bet and lost."

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My name is Clare and I’m twenty-two. I’m what my boyfriend now calls a cock whore I can’t seem to get enough of it now. I love to cum on a man’s big cock. I love to suck cock as well. I want to share how it started.

We live in a trailer park outside of town, it’s not a manufactured home community. Let’s call it what it is. There are about twenty other trailers in this park. It’s a cheap place to live while we try to get our shit together.

I’m 4’7” and weigh ninety pounds. I have small perky breasts and blonde curly hair that just passes my neck. I’m a very shy person, but that doesn’t stop the perverts from staring at me. It used to get old, all these pervy old guys asking me what high school I went to. But I won’t get into all of that.

I work as a medical assistant at a pediatricians’ office. It gets a lot of jokes at the office. Funny how people see me and think I’m a patient.

My boyfriend Justin is a great guy, and we’ve been together since I was sixteen. He’s tall and strong and has a nice cock, I think I love that the most about him. I love when he drives me hard from behind and slaps my tiny ass. Makes me cum screaming every time.

Last week he bet his boss on a football game and lost. But that’s not the worst part. He bet his boss me. He didn’t want any money. Denny wanted me. And not for a lap dance, or to clean his house.

His boss Denny is a big, husky man. Taller and bigger than Justin. He’s the guy that everyone goes to when they need something. He’s been running the company for a long time, and he’s well respected by his crew. Denny has a beard, but it’s short and well-groomed. Blue eyes and light blondish white hair. He’s an attractive guy for being much older than I am.

When Justine told me what his boss wanted, I cried. How could he do this to me? What the fuck was he thinking? Betting me! I was so pissed, I didn’t know what to do. Justin was the only man I’ve ever been with my whole life. I didn’t want him to lose his job over this or get in any trouble. So after a lot of thought, I decided to just go through with it.

The week flew by and Saturday finally came. Denny had invited us to his place. A nice house on the north side of town. It was back in the woods a little. Long porch across the front of it. A nice big open room that had a couple of deer heads and big game fish on the walls.

Denny offered us some drinks, as we walked through the door. I had a whiskey sour, and Justin had a beer. We sat on the couch as Denny finished up on the food he was preparing for us.

On the surface, I was trying to look relaxed. But inside my heart raced, my mind was going a thousand miles an hour with everything that could happen. I was holding Justin’s hand tightly as he kept telling me to relax.

Denny sat down next to me and turned the game on. He asked me if I was alright with this. I just nodded my head in affirmation. But deep down, I wasn’t so sure. But if this meant Justin wouldn’t lose his job, what choice did I have. I don’t think it would’ve come to that, but I didn’t want to risk it.

The room was really warm, so I took my jacket off. I was wearing a sweatshirt and black leggings. They made my legs look even skinnier than they were. But I wasn’t really trying to impress Denny. I think he knew that as well. Denny and Justin went to the kitchen to get some food. My stomach was turning so I declined his offer. When Justin came back, he told me to go see Denny in the kitchen for a minute.

My pulse quickened. My legs were shaky as I got up and slowly walked into the kitchen. Denny was standing there holding a plate of food. He set it on the counter and asked me to come to him.

Denny is much taller than I am. I only came up to his chest as he gave me a hug and kissed the top of my head. He asked me if I was alright with this. I told him I was, but I wasn’t looking forward to it. It made me feel like I was cheating on Justin.

He understood and asked, “What if Justin was in the room with us?” I was a little curious why he’d ask that. He looked down at me and told me to think about it. “If you’re alright with that idea, give me a blowjob on the couch right next to him,” he told me, then he walked back out to the TV room.

I went to the bathroom and splashed some cold water on my face. “What am I doing?” thinking to myself. I collected my thoughts and went back out to sit between Justin and Denny. I winked at Denny and licked my lips. He grinned and sat back further into the couch.

I leaned in and kissed Denny on the lips. He grabbed my little ass and pulled me up into him. My hand went for the front of his pants and I rubbed what felt like a huge cock under his jean zipper. I pulled at the button on the waist and tugged his zipper down.

I could feel Justin behind me moving around. He was probably adjusting his pants. But I wasn’t worried about him. I wanted to see what Denny had in his pants. I reached into his pants and placed my hand on… A monster of a cock!

Denny had a huge cock! It had to be at least ten inches long and about two inches wide. I could barely fit my hands around it at the base. I lowered myself down to get a closer look. Holding Denny with both hands, my ass pointed towards Justin. I kissed the head of his cock.

Denny moaned as I gave it another kiss. I licked up and down the side of it, then opened my mouth. I could barely fit it in my mouth. I swirled my tongue around the head and tried as hard as I could to get as far down as I could.

I spit on his cock and slapped it on my face. Denny moaned even louder as I stroked his giant cock and sucking on the head of it. He held my hair back while I bobbed my head up and down the head stroking the rest with my hands. Denny rubbed my ass with his other hand and found the wet spot that was building up between my legs and working its way through my tight leggings. I moaned when his fingers passed my labia and rubbed my clit.

I took his cock as far as I could in my mouth as he rubbed my clit harder. I slid my hand down his shaft and rubbed his balls. His balls were big and heavy in my hand. I licked his sack as I heard him gasp for air.

“Holy shit, kid,” he moaned out as my hand rubbed the head of his cock. I licked his balls and kept my tongue on his cock all the way back up to the head. I wrapped my lips around his cock again and started to suck him off harder.

I don’t know what exactly came over me. The feeling of Denny’s huge cock in my mouth. Or the fact that my boyfriend was right behind me watching. But my pussy was on fire and I wanted it to be filled.

I stood up and pulled my top off. Throwing it at Justin, I turned around and pulled my leggings and panties off. I felt Denny’s eyes lock on to me as I straddled him and rubbed his cock on my pussy. I lowered myself down but the pain of his cock was too much at first. I quickly came back up and rubbed it on my labia to slick it up some more. I held the base of his cock and watched the head slide into me. It felt amazing.

Denny put his big hands on my ass and helped me lower myself slowly. I couldn’t take all of it at first but with a little time, it was almost completely in me. I could feel his cock opening me like I’ve never felt before. I was on the verge of cumming when I felt it fill me to the hilt.

I closed my eyes and gasped for air. Letting out a little moan, I leaned into Denny’s chest. He put his arms around me and held me there for a moment while I slowly pumped my hips on him. “You’ve got a world-class pussy there, darling,” he whispered in my ear.

I knew it wouldn’t take long before I came. I put my hands on Denny’s shoulders and started to ride his cock. His hands cupped my ass to keep from going too far down, but as soon as I started bouncing harder on his cock he put them on my waist. He held my skinny waist as I bounced on his huge cock.

The first wave hit me like a flash of heat. I screamed out and flung my head back wildly. I kept riding, and before I knew it another more powerful orgasm was rocketing up through me.

Denny held my waist tighter as I felt him release his load into me. Causing the third orgasm, so intense I dug my fingernails into his shoulders and bit my lip. I didn’t want to stop. His warm cum had filled me to the point I could feel it oozing everywhere.

I started to shake again, I rubbed my fingers on my clit. And the forth intense orgasm ran through me. I felt chills up my spine when Denny took my nipple in his mouth and sucked on it. I fell into his chest. I was gasping for air, sweating, and completely drained.

I was so immersed with Denny, I had totally forgotten that Justin was watching. I just looked at him as he played with his cock. He looked a little lost for words, so I told him to slid over.

I leaned towards him with Denny’s cock still in me and wrapped my lips around Justin’s cock. Justin must have enjoyed the show. It felt like he was about to cum, but I wouldn’t let him. I didn’t let Denny out of me, as I felt him grow even harder again.

Justin was going to take his pants off, and I told him to sit back down. His look of disappointment made my pussy start tingling again. I drove my hips back and forth on Denny’s cock which was now totally hard again in me. And then told Justin to lay on the floor face up.

I rode Denny until I could feel his cock start pumping another load of cum into my petite little pussy, as the now fifth orgasm washed over and through me. I climbed off his cock and stood over Justin’s face and straddled him. I pushed Denny’s cum all over his face from chin to forehead. Justin resisted at first, but I reached back and grabbed his cock and told him if he ever wanted it in me again, he’ll do what I say. His tongue came up and licked my swollen pussy lips as the cum oozed out of it into his mouth.

Denny looked at me with a convinced look on his face and clapped his hands quietly. I had just cucked my boyfriend for making me fuck another man. I grabbed Justin’s hair and pulled his face deeper up to my pussy until his mouth and tongue worked out every drop of cum Denny pumped into me.

I fell forward on the floor when I was satisfied with Justin’s work. He slid out from under me and took a big swallow of his beer. Denny laughed at him and asked him if that was the chaser.

I laid down flat on my stomach, as I turned to look at Denny. I blew him a kiss and licked my lips. Denny leaned forward and tapped his big hand on my ass cheek. “Mighty fine work there, little lady,” he said as he laid back on the couch.

I smiled. “We’re not done here yet.”

Published 4 years ago

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