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My Crush

"How Roger became a cuckhold"

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Here I am in my thirties, still single, and all my friends are married.

It can feel lonely at times, even though I still have fun, but the dating scene is very frustrating.

Years ago, I came close to getting hitched. She was a college sweetheart. We used to fuck like rabbits at any time, anywhere.

I remember feeling anxious about how things started to unravel between us one night at a party.

Ava started flirting with some of my friends.

We both got drunk, I pulled her aside and asked, “What's with you tonight, Ava? Do you want to fuck my friends or something?”

She almost fell over drunk and said, “Sure, I would love to fuck some of them, but only if you watch.”

Two of my friends heard this, and one of them said, “Hey, Roger, that sounds like a good idea. You can watch me and Eric fuck your girlfriend.”

Ava handed me another shot of whiskey and said, “Drink up, Roger, and watch.”

By the time I drank the shot, my two friends Eric and Doug had their hands all over Ava.

I watched as they carried her to a bedroom. I followed, and they had her stripped naked in seconds.

Eric looked over at me and said, " Hope you don’t mind, Roger.” Then handed me a bottle of tequila.

Doug shoved his cock into Ava’s mouth, and she went right to work on it. Eric knelt and began eating her.

I could hear muffled moans from Ava as he ate her.

Doug looked over at me and said, “Fuck you're lucky, Bill. She sucks cock like no other.”

Eric stood up and unzipped his pants, and I watched as he slid his cock into Ava’s soaked pussy.

I saw Ava’s eyes almost pop out of her head when he shoved the entire cock into her.

Ava's head flipped backward as Eric pumped her pussy like a crazy man.

Eric looked at me and said, “Fuck she is tight. If she were my girlfriend, I would fuck her three times a day.”

Doug said, “Hurry up and cum in her, Eric. I want my shot at her hot pussy.”

Eric smiled, looked at me, and said, “Time to breed your girlfriend, Roger.”

I watched as he filled up Ava’s pussy with his cum.

Doug did not wait one second before he shoved his cock into her cum soaked pussy and began fucking her.

Eric, along with me, watched as Doug fucked her. Ava was having the time of her life with so many paying attention to her and fucking the crap out of her.

It only took another minute before Doug shot his load into her. He looked over at me and said, “I think she is ready for your cock, Randy. At least you should clean her up.”

I said nothing and went home, and that was the end of that relationship.

When I got home, the thought of cleaning up Ava made me hard as a rock. I kept thinking I should have done it. I went and sat on my couch and replayed what I saw in my head and jerked off. It only took a few minutes before I shot a load of cum all the way up to my chin.

I had never tasted my cum before and thought maybe I should, so I did. I did not mind it at all. In fact, I liked the saltiness of it.

I had a few more girlfriends in my life, none of whom I thought were wife material, or at least not long-term girlfriend material.

…………………………….

That brings me to my life today. The only woman that I have had any interest in is married to my best friend, Jimmy. Carolyn is a petite blond with perky tits and a body to die for. I have wanted her for years. I had a crush on her for so long.

Every time I see those two, all I do is dream about fucking her or at least cleaning up her pussy after Jimmy fucks her.

I am the third wheel sometimes when the three of us go out together. Jimmy and Carolyn both have tried to set me up with someone, but it only worked out once.

Her name was Nancy, and we went out together for a couple of months. She was great to have sex with.

She would blow me at the drop of a hat and do it anywhere. I remember once she was horny and wanted my cock in the worst way, and pulled it out while I was driving.

I pulled off the freeway and parked under a tree, and she got out and pulled down her pants and said, “Fuck me. Fuck me good.”

I stumbled getting out of the car as my cock was still hard and poking out of my pants.

She bent over on the side of my car. I fucked her as I watched cars go flying by on the freeway.

I thought we were concealed from the road, but when a semi-truck drove by, he tooted his horn.

Nancy looked over at the road and said, “Fuck him. Don’t you dare stop.”

I looked down at her ass as I was fucking her and pulled out my cock and shot a load of cum all over her ass.

I loved sex with her, but she became so clingy that I could not do anything without her, and I asked her one time to give me some space, and that was the end of that.

So, for now, I am just the third wheel with Carolyn and Jimmy.

I enjoy going out with Carolyn and Jimmy, and I let my mind wander about having sex with Carolyn. I often wonder if she knows I am undressing her with my eyes.

One night after dinner, Jimmy suggested we take a dip in their pool. I was so excited that I would get to see Carolyn in her bikini, but I hoped I would not be too excited so that it would show my cock as hard as a rock.

Jimmy loaned me one of his bathing suits, and I walked out into their backyard to see Carolyn and Jimmy already in the pool.

I jumped in and joined them, and it was all innocent in the beginning.

Jimmy got out of the pool and brought a pitcher of margaritas poolside for us. We drank the first one, then a second, and all of us were getting a little drunk. 

Jimmy then asked me, “Tell us all about what went wrong with Nancy? I thought you two hit it off, and you told me sex with her was fantastic.”

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I turned a little red with Carolyn looking right at me, and I replied, “The sex was great with her, but she became too clingy. I think she wanted to get married soon, and I was not ready for that with her, but I do miss the sex.”

Carolyn looked at me, and I think the liquor was talking when she asked me, “What was your favorite position? How often did you two have sex? What do you do now for sex? Just masturbate?”

Jimmy interjected and said, “Now, Carolyn, that is very personal. I don’t think he would want to answer all of that.”

I said, “I don’t mind answering. We had sex a few times a week if possible. I liked eating her and loved when she would blow me anywhere, and yes, sadly, all I do now is masturbate. If I am being perfectly honest, sometimes I masturbate to thinking of you two fucking, and I am watching.”

Jimmy looked over at me with a little sparkle in his eyes and said, “It would not bother me to have you watch us. What do you think, Carolyn? Want to fuck so our friend can watch?”

She laughed and said, “Sure, why not. This might be fun.”

I could not believe my ears. Was I about to see my biggest fantasy come true? To see her naked and watching her get fucked.

They both stood up, and Jimmy said, “Give her a kiss before the show.”

I held Carolyn and kissed her as Jimmy watched.

Jimmy took Carolyn by the hand and led her to their family room.

He turned around and saw me standing in the same place and asked, “You just going to stand there? I thought you wanted to watch.”

I was in a daze, and when I heard what he said, I ran to their family room.

Jimmy pointed to his couch and said, “Sit there and watch Carolyn strip for us.”

I watched as she took off her bikini. First, the top came off, exposing her perfect, perky tits. I just knew they were going to be perfect.

She walked over to me and handed me her top, then took off her bottoms and handed those to me.

I am sure I was drooling looking at her racing stripe leading to her pussy.

She laughed and walked over to Jimmy, saying, “Ready, lover, to put on a show?”

She knelt in front of Jimmy, pulled down his swim trunks, took his hard cock into her mouth, and began sucking on it.

I could not help myself and pulled out my cock and began masturbating.

Jimmy pushed Carolyn to the ground, and they got into a sixty-nine position.

I watched as he parted her lips and ate her sweet pussy. God, how I wish that were me eating her.

Jimmy looked over at me and said, “Enjoying the show there? Why don’t you get a little closer and watch me plunge my cock into her pussy.”

Carolyn lay down on the floor, and Jimmy mounted her, and I was only inches away from her as I saw his cock bury deep inside of her.

Her sweet scent filled the air as I saw Jimmy's cock glisten with her juices.

He went faster and faster, and Carolyn began moaning with pleasure.

Jimmy said, “Watch this.” Then he flipped her over and began fucking her doggie style.

My cock was as hard as it ever has been as I watched.

Jimmy saw me and said, “Slide underneath her. Get right below her pussy so you can see my cock go in and out of her.”

I got down in front of her and pushed myself below her right by her pussy and watched Jimmy's cock slide in and out of her.

I stuck out my tongue in the hope that some of her juices would fall on it.

Jimmy began grunting and said, “Thar she blows.”

I watched as he pumped her full of his cum.

Some of the drops of cum fell onto my face.

Jimmy saw this and said, “Why don’t you be a good boy and clean up, Carolyn. I know she needs it.”

Carolyn moved just enough so she could sit right on my face, and she said, “Now do it good, Roger. Clean me up, and if you're a good boy, I will suck your cock till you cum.”

She rubbed her pussy on my face for some time, and as far as I was concerned, it could have been forever. I did not mind Jimmy’s cum mixed in with her juices.

She had an orgasm, and her juices flowed into my mouth.

She finally stood up and wiggled her finger to come over to her, and she then knelt and took my cock in her mouth and began blowing me.

I wished I could have lasted longer, but within a few minutes, I exploded a load of cum down her throat.

She got up with my cum still on her tongue and then kissed me and deposited all my cum down my throat.

Jimmy watched and said, “Did you like that, Roger? Do you ever want to do it again?”

I replied, “Are you kidding me? I would do that five times a day if we could. Fuck yes, that was the best time I have ever had.”

We all went and had another batch of margaritas.

Jimmy got hard again, and I watched as Carolyn blew him, and after he came in her mouth, she came over to me again and kissed me so I could have all of Jimmy’s cum.

We all fell asleep on the floor in the living room, and I was the first to wake up the following morning. I sat in a chair, marveling at Carolyn's body.

I loved her freckles. Her lips, her pert nipples, her nose, just everything about her, and I could not believe I got to taste her pussy.

Those two woke up, and we shared some breakfast and talked a little about what happened.

Jimmy said, “Now look, Roger, that was a ton of fun last night, but don’t get any ideas about fucking Carolyn or having her give you blow jobs. Fucking her is my job, and pleasure, but if occasionally you want to stop by and watch us again, I am sure we could do that.”

……………………….

Every third Saturday of the month, they invite me over for another pool party. I get to clean up Carolyn, and most of the time she either blows me or jerks me off after I get done with my cleaning.

My life is the best it ever has been now.

Published 
Written by AAnna
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