She Cheats With His Best Friend

14 min read

photo: SexArt

A cuckold tale from three points of view

JERRY: I went to college with Dan. He got me a job out here in LA and we actually have offices next to each other. He’s technically my boss, which is awesome. Since he’s my best friend I do very well each year at review time. And whenever I need time off I just take it.

One night at our house I was giving Dan a hard time about his pot belly — we’re 40 now and it’s starting to show.

“Leave Dan alone,” my wife Sarayah said. “I’d do him.”

Everybody on the back porch where we were sitting around drinking and talking kind of ignored that comment. But I didn’t. Neither did Dan, apparently.

“My wife said she’d do you,” I said to him at work the next Monday.

“Yeah,” he said. “That’ll teach ya to insult my beautiful body.”

I could tell he was kind of proud of himself, now that my hot wife had declared that he was fuckable. Dan was single these days. His first marriage hadn’t worked out, and now he was Tindering and having a heck of a bad time of it. I was glad Sara had puffed him up a bit. I was also incredibly turned on. I didn’t say anything to Dan or Sara about it, but for about a week afterwards I masturbated thinking of my wife and Dan making out — they had once, at our tenth wedding anniversary party! They were both drunk. And I thought about them doing more.

Finally I hit on a plan. It was going to be part prank, and part cuckold fantasy come true. If only Sarayah would go along with it. Something told me she would. We had gotten into a kind of rut, sexually, since the kids. I was thinking she was as game to try something new as I was.

“Listen,” I said to her, “you know you told Dan that you would do him, right?”

“Oh shit,” she said. “I’m sorry. I was drunk.”

“It’s alright,” I said. “In fact, it’s given me a great idea for a prank. What do you think of this?”

I explained to her the plan. You have to understand that even though Dan is my best friend, Sarayah and I do like to make fun of him sometimes, because he thinks he’s so hot and he thinks he’s god’s gift to women, but he’s obviously not, because he’s divorced and alone. The reason he’s divorced is that he thought that he deserved more than just one woman, if you know what I mean. But now he has no women, ironically. He still thinks very highly of his handsome Mediterranean dark looks, though. And my wife and I find him to be funny and pompous sometimes, that’s all, so we make fun of his swagger.

“I love it,” my wife said when I had finished telling her the idea. “But do you want me to actually follow through on it?”

“Sure, if you want to,” I said.

The idea was at the next get together for Sarayah to throw another compliment Dan’s way, and then take him aside and tell him this:

“We never get to spend any one on one time,” she was supposed to say. “It’s always with a bunch of other people around. I’d love to just have a coffee with you alone some time.”

We laughed our heads off at this idea, because we knew what this would do to Dan’s head. He wouldn’t be able to get through the door after he heard this. It’s exactly what he fantasizes every woman wants from him — an assignation. A secret date.

“Oh my God, that’s hilarious, Jerry,” she said. “I’ll do it this Sunday at Jen’s Superbowl party.”

“Perfect,” I said. “Oh, and you have to add this — don’t tell Jerry. You know how jealous he gets.”

“Of course,” she said. “He’ll love that. Sneaking around with his best friend’s wife.”

It’s true that Dan had no morals when it came to fucking. He fucked my girlfriend in college. He wasn’t even that sorry about it. He fucked around on his wife. He doesn’t consider it immoral.

“It’s just desire,” he said to me once. “It’s not a crime.”

Anyhow, I couldn’t wait for the Superbowl. I jerked off a bunch of times imagining how it would play out. I knew this. If my wife asked him for this secret coffee at the Superbowl party, it would for sure be followed by an attempt to make out with her at least. Once you light the fire in old Danny boy, it doesn’t go out easy.

So in my imagination I would be hiding behind a bush in Jen’s backyard when my wife Sarayah goes up to say goodbye to Dan. And he would grab her hands and look at her and say one of his super schmaltzy lines. He is the schmaltziest, but I have to say there are some chicks that like that kind of talk. He says things like, “I don’t know if you will ever render me the treasures of your body, but just one kiss from you would be divine.”

In my masturbation, he says that, and then Sarayah and he have a bit of a smooch. And she puts her hand on his crotch and tells him how much she’s looking forward to that coffee, but warns him again, don’t let Jerry know, he’ll kill me.

And of course, what I was really looking forward to was seeing him the next day in the office, now that he was in the process of trying to seduce my wife, and would actually have a coffee date set. I couldn’t wait to see his phony smile, and watch him slap me on the back nervously, trying to pretend that it’s all ok and we’re still best buds. It was going to be pretty funny.

So the Superbowl came. I was really getting into the game, it was a close one. And as the Patriots came down the field for their last attempt to tie things up, Sarayah came over and said, “It’s done.”

It took me a moment, then my heart leaped. She had done it!

“So you made a date?”

“We’re gonna go out for a drink after work this Wednesday. He’s gonna come by my work. I told him you have boxing that night. It’s perfect.”

“Oh my God,” I said. “How awesome. Was he surprised?”

“His eyes kinda popped out,” she said. “He said he’d love to have a drink with me. He actually said, ‘Angels and ministers of grace defend me, I must be dreaming.’”

“Oh yeah, that’s from Hamlet,” I said. “He says that all the time these days.”

“Then he kissed me,” she said, blushing slightly.


“Oh the lips, where do you think, stupid?”

“No, I mean, where were you? Did anyone see?”

“We were in the backyard behind the swing set. Nobody saw us.”

“Oh my God. How long was the kiss?”

“It was pretty long,” she said. “I was starting to get nervous so I pulled away.”

“That fucker,” I grinned. “Kissing my wife while I’m in here watching fucking football.”

“I’m sorry,” my wife pouted.

“Sorry?” I said. “Look at this?”

I pointed at my crotch, where my erection was pressing out, visibly.

“Oh my, we’ll have to do something about that when we get home.”

We fucked like crazy. I said some of Dan’s pretentious phrases while I was fucking her and cracked her up. It was a ball.

And when I went into the office on Monday, the prank really paid off.

“Here you go buddy,” my best friend said with a big fake smile. “Look what I got us — front row!”

It was a ticket to System of a Down, the band we used to love when we were in college.

“Damn!” I said. “Those were expensive, let me pay you.”

“No, it’s my treat, buddy,” he said.

Yeah, no kidding. It was my treat that he was trying to snack on — specifically my wife. And it did give him this real phony, smug, satisfied look, just as I predicted.

This prank was going even better than I ever thought it would.

Who knew the whole thing was about to blow up in my face.

SARAYAH: So this was the crazy plan. I was supposed to go out for a drink with Dan, my husband’s best friend, and then bring him back to our apartment. I was going to tell Dan that Jerry was going out with some friends from boxing and wouldn’t be back until late. This was going to be tricky, because Dan has his own place and why wouldn’t we just go there? I would tell him that I didn’t want to Uber all the way out to Highland Park. Or something.

And then we were supposed to get into our bed and start foreplay, and then Jerry was supposed to come in the front door and catch us.

I guess the idea was that we would then reveal that the whole thing had been a prank, and that we were trying to teach him a lesson or something.

But of course, it didn’t work out like that. Because, surprise, surprise. The date went pretty well, and I was enjoying being out with Dan. And I was loving the idea of cheating on Jerry with his permission more or less. And at the bar Dan started really turning on the charm, kissing my hand, and then making out with me really intensely.

“Don’t you feel a little bad about Jerry?” he asked at one point, pulling away.

“No,” I said. “Jerry never needs to know about this. I want to have one night with you, Dan. I’ve always fantasized about it. I want to see if it’s as good as my fantasies.”

And then I kissed him real sweetly.

“I’ve always had a crush on you too,” he admitted. “But I never dreamt, I mean… Jerry’s my best friend.”

“Yeah,” I said. “But what can we do.?The heart wants what the heart wants.”

“And what does your heart want?” he asked me, pinning me down with his eyes.

“My heart wants you to fuck me,” I said. “Let’s go.”

We got into an Uber. And we went to Highland Park. Dan’s house. I knew Jerry was going to be pissed. But something came over me. I wanted Dan to myself.

I was pretty turned on. I hadn’t been with another man since I met Jerry, fifteen years ago. There had been one guy at work who was sort of like a work spouse, and at a convention we made out, but he was married and he pulled the plug on that real fast, and got himself transferred to San Francisco. I have a slightly slutty side, I guess. It really comes out when I drink. And the wine I had drunk that night with Dan was very velvety and good. I was feeling a nice buzz. And the idea that I was actually going to go home with this very handsome guy, it was sort of crazy and I could hardly believe it was happening — it was almost like I was watching it in a movie or something. In the Uber he started kissing my neck and putting his hand up my legs, touching me between my legs.

“Stop, the driver’s right there,” I whispered to him. And he pulled it out, but I was very wet. I snuck my hand over to his crotch and felt the bulge. He was hard. Jerry had told me that Dan had a big dick. It’s not that Jerry was small, but I guess I had always preferred a really big dick. My high school boyfriend was large. And my college boyfriend was larger. Then I met Jerry, who was average, but he was the love of my life so I forget about big dicks. But lately, I guess when he fucked me it didn’t feel all that overwhelming any more. And I sometimes remembered what it was like to be filled up with an eight or ten inch dick. It is totally overwhelming, and I lose control. I guess that was it. I didn’t lose control with Jerry. And I didn’t know exactly how big Dan’s dick was, but I really wanted to be overwhelmed, and now it seemed to be about to happen.

It was like a fantasy coming true. And even though Dan was occasionally ruining it with all his flowery language and bullshit, my mind kept coming back to that big bulge in his pants and I was getting hotter and hotter, just wishing the Uber would hurry up so I could tear those clothes off and jump his bones.

Finally we got there and we ran into his house.

“I want to render you the treasures of my body, Dan,” I joked with him.

But pretty soon he was laying on that charm so smooth that I forget about making fun of him and lost myself in the moment.

“These breasts,” he said, as he took off my bra and started kissing my tits. “These breasts that have launched a thousand ships. Helen of Troy is homely next to you, beauty.”

Oh my God, I thought. Helen of Troy! But he was sucking my nipple so tenderly, like he couldn’t believe his luck. It went to my head, I have to admit. I started feeling like some exotic sex goddess in his bed. It was what he wanted, I guess. And I wanted it too.

“These thighs,” he said, as he pulled down my skirt and started kissing my thighs. “These thighs are tastier than ambrosia, the food of the gods. You’re making me immortal by granting me access herein.”

“Herein!” I said.

I had never heard that word “herein” uttered during sex, that was for sure.

“Like Leander who swam across the waters to be with his Hero, I have braved the waters of long friendship with Jerry and arrived here, at this altar, to worship you, divinity.”

And with that, he pulled down my panties. I couldn’t believe my husband’s best friend was pulling down my panties. I was so horny, lying there on his bed, now naked before him, thinking of that huge hard cock that was going to be in me in a minute. I almost came as he sat there gazing at my pussy in wonder, like he was looking at some cliff in Yosemite or something.

“Awe and wonder,” he said. “Wordsworth, Coleridge, and even Shelley have ne’er felt anything approaching the awe and wonder I feel, to finally gaze upon this paradise.”

“Ne’er!” I thought. Another one I’d not heard in this particular context. And yet, as his hand slowly reached out to touch my pussy, I do believe I was trembling with lust.

“Oh baby, yes!” I screamed, as he put his finger inside me. Then another finger. Then a third. And he started penetrating me with his fingers and his intense gaze, beholding me like he was beholding a heavenly vision.

“If this is wrong…”

“Then why does it feel so right!” I said, finishing his sentence. “Fuck me! Fuck me now!”

He pulled off his jeans. I saw that big hard cock. It was beautiful. I could hardly contain myself. In a minute it would be mine!

He got on top of me, and was about to slip it in, when —


His doorbell rang.

He looked at me in alarm. Who could that be?

Oh no, I thought. Because I had a feeling I knew exactly who it was.

DAN: I was about to fuck my best friend’s wife. My dick was throbbing. I had never wanted anything so bad. It was the one pussy on earth I shouldn’t be fucking. And it was the one pussy on earth I wanted to fuck. And I was about to get what I wanted, when the door bell buzzed.

“I’ll be right back,” I told her, and I threw on my robe and went out to see who it was.

“Jerry!” I said. “Holy shit! What are you doing here?”

“Dan, aren’t you going to let me in, shit it’s cold out here.”

I let him in. And I said very loudly so that she would hear me in the bedroom and not do anything stupid like come out, “Jerry my buddy, come into the kitchen, let me get you a beer.”

Once I got him in the kitchen and gave him his beer, he explained that he was looking for his wife.

“I think she’s cheating on me somewhere,” he said. He looked really anxious.

“Why would you think that?” I asked.

“I don’t know, Danny boy, why would I think that?” he said, and he looked at me real funny.

“What are you talking about?”

“I don’t know, Dan, what am I talking about?” he said again, and now he was looking at me even funnier.

“I have no idea,” I said, and I could hear my voice cracking. I was actually starting to get scared. I mean, Jerry had been doing this boxing thing for like five years, and I knew he could knock me out with one punch. But how the hell did he know?

“Are you fucking my wife, Dan?” he asked straight out.

“No!” I said, innocently. After all, I hadn’t fucked her yet. I was about half an inch away from fucking her, but technically…

“Not yet he’s not,” I heard a voice say. “But he was about to when you rang the doorbell.”

I turned around and there she was, naked, standing in the kitchen. Man she looked good. Like a model. Big tits. No fat on her. Nice pussy shaved with just the bacon strip on top. She was exactly as I pictured Venus, herself, the goddess of love. My heart melted.

“Sarayah!” I gasped. “What…”

“Take it easy, big boy,” she said and she came over to me and put her arms around me. “Jerry knows all about us. I was supposed to bring you back to our place so he could watch you fuck me, while hiding in the closet. But I changed my mind about that and came back here so we could have some privacy. How did you know, Jerry?”

“Oh, I was spying on you at the bar, and then I followed you out here.”

I looked at my buddy. He had this big smile on his face, like, “I got you!”

“You mean, you want me to fuck Sarayah?”

I couldn’t get my head around it.

“Yeah, I’m a cuckold, Dan,” he said. “Don’t worry, I won’t beat the shit out of you, I promise.”

“Oh man, I feel so much better,” I said. “I was starting to feel pretty crummy about all this, to tell the truth.”

“Really?” said Sarayah, skeptically. “You looked like you were having fun.”

“Well, I was, but…”

“Let’s get back to it then,” she said, and she grabbed my hand and led me back to the bedroom. I sat on the bed with a limp dick.

“Oh, poor boy, what happened to that big hard on,” she said, and she got on her knees and started sucking on it. Sarayah has really nice thick lips. I had never felt a blowjob like that before. It was like my dick was being sucked up into a vacuum cleaner. And my best bud was there in the doorway watching, jerking off.

“Jesus, this is weird,” I said.

“In a good way?” asked Dan, from the door.

“I guess so… shit.”

Now that I was hard, Sarayah pushed me down on the bed and got on top of me. Finally I was in that sweet pussy of hers.

“Oh yeah, Danny boy,” cheered Jerry from the door. “I’ve fantasized about watching this for a long time.”

His wife was moaning with pleasure.

“Is it good, honey?” Dan asked her.

“Oh my God, so good,” she said. And then she started screaming as she pounded down on me harder and harder. I think she had an orgasm, because suddenly she collapsed on top of me after a bunch of really loud screams. I pushed her off me, and got ready to fuck her from behind.

“Oh yeah, Danny, good idea,” said Jerry, as she got on all fours, and I entered her from behind. She had a very sweet, round ass. And then she was screaming again.

“I’m cumming, I’m cumming, oh yeah, fuck me, I’m gonna cum!” she screamed.

And then I really hammered into her and pushed her over the edge and she collapsed again on the bed. I turned her around and fucked her from the side. I saw Jerry come over from the door and join us on the bed. He got on the other side of her as I fucked her.

“Are you having fun, honey?” she asked him.

“Oh my God, so hot,” he said. “Thank you.”

The two of them started making out. I continued fucking her and started thinking about it. I guessed this had been a plan of theirs for a while. I felt kinda bad that Jerry never said anything to me, and just let me kind of twist in the wind as his wife came onto me. But I understood. It was part of the thrill for him, it made it more real.

“Mind if I cum in your wife, Jerry?” I asked him after a while.

“Go ahead,” he said, and gave me the thumbs up sign. I let go in her and felt a big load of cum shoot up in her.

I lay there exhausted.

“My turn,” said Jerry, and he got on top of her and started fucking her. He had this loving look in his eyes like she was the most precious thing to him. Like he was really close to her and she was close to him. Like they were still in love after all this time.

I was jealous. I wished I felt that about somebody. The way Jerry felt about his wife. I mean, I really loved fucking her. But Jerry, as he fucked her, he looked so happy. He was smiling.

“I love you so much,” he smiled, and then he came in her.

“I love you, too, honey!” she said.

It was sweet. It kind of gave me something to shoot for, I guess. I just had to keep looking. Eventually, I would find a crazy slut like Sarayah who would do anything for her man, even if it meant fucking his best friend. Not that I would like that.

I guess there are two types of guys; guys like Jerry who like to watch their wives get fucked, cuckolds they are called. Jerry explained it to me afterwards after the three of us got dressed and went back outside for a nightcap. Then there are the bulls, the guys who do the fucking.

I was a bull.

After they left, heading home to their life together, I felt kind of lonely again. I looked at myself in the mirror, though, and I looked good. I had a big thick cock. I had some muscles. And I had that manly look in my face.

“Hello, Bull,” I said to the mirror.

And I laughed.

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