She Cheats With His Best Friend

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.

“Where?”

“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.