Two Men Cuckolded in One Night

8 min read

photo: SexArt

My girlfriend Emily has gone up to Napa on a road trip with her friend, Sally O’Sullivan. Irish much? Anyhow, Sally likes to drink wine and have a good time. She’s got a boyfriend, Dirk. Emily told me she was going to explain cuckolding to Sally on the trip and see if she felt like cuckolding her boyfriend.

Maybe it would be a double cuck! Was that a thing?

At this point, Emily hasn’t even single cucked me yet. We have played with it for almost a year now. Role playing her cucking me. Sometimes I’m watching, sometimes she’s just out being her free self. Cheating on me.

Those role plays have been so arousing.

And now, here I am in Los Angeles, watching their progress on my iPhone. I can check her location. I know she’s driven from Napa to a plaza in Sonoma with bars and restaurants.

It’s a beautiful summer night and she is hanging out in what she said, in her text, was like a Beer Garden of Vermont meets California.

And she sent me the first pix of the guys they met.

Photo by Austin Distel on Unsplash

I don’t know, it’s pretty far away, but I’d guess Emily would go for the one in the white pants. She’s always lusted for the big personalities, maybe because mine is so subdued.

I’m a very mellow computer programmer, a home body, and kind of passive, I guess. That’s why I think this role of passive bystander while my girlfriend has an adventure will be so fun.

And now it’s maybe happening. I don’ t know. I’m in bed. It’s 9:20 PM. And I’m in a real state of euphoria. There is a tingle rising up from my groin area into my brain, and then this tingle seems to go back down and circle back up to the brain, in a kind of track. And it goes around and around.

This must be chemicals and hormones warning the animal that is my body that his mate is being sniffed by another. These hormones in the primitive world, I suppose, would have spurred me into action. I would have grabbed my spear or my club and gone chasing after this other.

But in this modern world, the hormones just course through my passive, resting body and send me on a really pleasant trip.

It’s like drugs. But better. There will be no hangover or physical consequences to this trip into ecstasy. I will wake up fit as a fiddle in the morning.

And tonight, I will travel so far into unknown realms of desire and eroticism. I will, maybe, experience what it’s like to let go of my lover’s hand. To release her into the pond. And let her dance and swim with another big fish.

That’s how my brain feels right now, like something is swirling around in it. Something colorful and beautiful, like a tropical sun fish.

I’m so happy.

Just waiting.

Should I beat off?

I don’t even need to. I’m in the half chub state just lying here. And the pleasure is circling, so why even touch my dick.

I’ll just wait for another pic, or another communication.

Maybe I’ll get the word. That something is on with this white pants. That they are connecting. That they have…begun.

At about 10:20 I got a text.

“Jordan, are you sure about this now?”

“Of course I’m sure!”

“OK, just checking. You’re not having second thoughts?”

“Absolutely not. You have complete freedom. A complete free pass. I grant you and certify you this leave, young lady. Please consider this my personal stamp and seal of approval of whatever you’re up to. What are you up to, by the way?”

“The guys came back to our suite,” she texted. “You want me to tell you now or you want to wait until…after?”

“Oh, please, whatever you prefer m’lady,” I said.

I don’t know why I adopted this hyper formal tone with her. It isn’t usually the way I speak to her. But something about this seemed to call for it. There was something very erudite and sophisticated about what we were doing.

“Well, the only thing I’ll tell you then is that Sally took Sergio to her bedroom. And Rudy is in here with me,” she texted.

“Are you having fun?” I said.

And she sent me the thumbs up.

Wow were the next three hours intense!

I did beat off, I must admit. Now that it was on, there did seem to be reason to satisfy myself. And wow, each time I ejaculated it shot higher into the sky. The idea of my girlfriend with white pants, it just sent it flying.

The phone rang. I thought it was her, with something new to report. I grabbed it. It was not a number I recognized.

“Dude,” said the male voice. “This is Dirk.”

Sally’s boyfriend.

“Hey, Dirk!” I said. “What’s up.”

“I just got a text from Sally,” he said. “I uh, I’m not sure what it means.”

“What does it say?”

“Well, I’ll show you. Can I come over? I really don’t want to talk to you on the phone about this.”


He just lived one canyon over. In ten minutes he was at my door.

“Well, thanks for letting me come over so late. I just got another text,” he said.

He showed me his phone.

The first message said, “We met some guys.”

“Yeah?” I said. “So?”

“Well, I thought that was pretty weird. Don’t you think that’s pretty weird?”

“I don’t know, Dirk,” I said, playing dumb. “I mean, a couple attractive young girls, up in Napa together, I figured they’d get hit on, didn’t you?”

“Well, yeah,” I said. “I was actually kind of hoping they would.”

I looked at him. He had a twinkle in his eye. Then he showed me the second text.

“Guess what?” said Sally. “Emily’s bf Jordan wants to be a cuck too! Can you believe it!”

I looked at him and I couldn’t contain my smile. I’d been outed.

“You too?” I asked.

He nodded.

“You been toying with the idea?” I asked.

He nodded. For a while now, apparently. But the last thing Sally expected was that Emily would feel the same way. Emily kind of projects a good girl vibe out to the world. Only those who really know her know how wild she can be.

“It’s quite a turn on, isn’t it?” I said.

“Like nothing else,” he enthused. “I get it real tight in my chest. And my throat. Regular sexual arousal is nothing like cuck arousal. I feel like I’m in heaven when we fantasize together about Sally with another guy.”

“Well, apparently they are with a couple guys right now,” I said. I showed him the text about coming back to their suite now.

“Oh my God, they’re already in the hotel room!” he cried, with excitement.

“Yeah,” I said. “And apparently your girlfriend went into the bedroom with this guy named Sergio.”

“Sergio!” he cried. “Perfect!”

He suddenly sat down on the couch and pulled out his cock and started masturbating.

“Oh my God! I’ve dreamed about this for so long, haven’t you!”

“Yes!” I said.

And I sat down next to him and pulled out my cock too.

“They’re with two new guys. They’re down to their bra and panties,” Dirk said.

“No,” I said, picking up on the fantasy. “Emily is in her own bedroom, and she has her bra off. And the guy in the white pants, Rudy, is sucking her tits.”

“What white pants?”

I showed him the picture she had texted earlier.

“OMG, you have pictures!”

“Yeah, I guess this is Rudy and this is Sergio,” I explained.

He looked at it, then he went back to spanking his dick.

“Sally is sucking that guy off. She loves to suck cock. She sucks it so good. Her lips are so luscious. The guy is like moaning and moaning.”

Then Dirk started moaning.

This was pretty weird, me sitting here jerking off with Dirk, who I didn’t know that well. I looked at his penis. It was pretty small, like mine. About four and a half inches hard.

“Those guys have such big hard dicks,” I said.

“Oh my god yes,” he agreed. “They’ve got like nine inch hard ons.”

“And they’re in the gym all the time,” I said.

I looked at Dirk’s arms. They were skinny like mine. I guessed he weighed about one hundred twenty, maybe ten pounds less than me. We were a couple of weaklings. And our women were with some real tough guys.

“Those guys could kick our asses,” he said.

“Yeah,” I agreed. “But they don’t have ten million dollars in stock options.”

I had heard that that’s how much Dirk got for programming. I myself got about the same for running a programming unit. We were both one hundred percent weakling nerds.

And rich.

“We might be rich,” he said. “But our girlfriends deserve to have a couple of real men fuck them.”

“You’re right,” I agreed. “They are awesome girlfriends. I hope they’re enjoying sucking those big dicks.”

“I’m sure they are,” he said.

I heard him yelling then and I looked over and he came. A little blob of cum popped out of the head of his dick and ran down the side.

“Wow,” I thought. “He cums even less than I do.”

“I bet Sergio is cumming a huge load in your girlfriend’s mouth now,” I said, as I continued wanking.

“Not a little drip like mine,” he said, picking up on my meaning right away. And without hesitation he started beating off again.

“I wish they’d sent us more pics,” he said then.

“Alright,” I said. “I’ll text her.”

I texted Emily. “Go to Sally’s bedroom and take a photo. Dirk wants to see.”

“OMG,” she texted back. “Dirk is with you?”


“Is he alright?”

I looked over at Dirk, who was pounding his small dick with a crazed look on his face.

“Never better,” I said. “But I think if you get him a photo his brain might explode.”


In a minute the phone dinged and I saw the photo of Sally and Sergio in the bed together. Neither of them had any clothes on. And they looked kinda pissed, like Emily had just interrupted their fucking.

“Here you go,” I said, and handed the phone to Dirk.

“Oh my God, they’re naked together,” he cried.

“I think they’re fucking dude, look at that guy’s dick.”

In the photo you could see that Sergio’s dick was fully hard, about eight inches, and very close to Sally’s pussy. Like it had just been pulled out.

“Oh my God!” he cried. And he came again. This time the little wad of cum shot up into the air like a jumping bean and landed on the side of my couch.

“Ew,” I said.

But then the phone dinged.

“Here’s a selfie of us,” the text said.

In the photo, the guy Rudy was kissing my girlfriend’s cheek, and she was smiling up at the camera.

My heart jumped.

Oh my God, another man kissing my Emily.

I came right away. A big gush of cum. Also on the side of my couch.

“Have Rudy take one from his POV,” I texted.

In a few seconds, I got the photo. The one. The image that was burned into my soul forever and ever. The most ecstatic moment of my life.

“He’s fucking me,” was the caption.

He’s fucking me! (Images licensed from Adobe)

And from Rudy’s POV on top of her, I saw my girlfriend. And I saw that look on her face. It was a look that of course she had never made with me. It was the look of “Oh my God you’re fucking me so good!”

In fact, in the next POV she sent, the caption just read, “Oh My God!”

Oh my God!

“Look at this,” I said, showing the phone to Dirk.

“God!” he said. “He’s fucking your girlfriend!”

“I know!” I said.

And we were both hard again, pounding away at our dicks.

What a strange way to spend a night, I remember thinking.

“Is it really happening?” I remember him crying over to me. “Are they really getting fucked.”

“Dude, they’re getting fucked good!” I said.

And I remember we both shot again.

Like the tenth of thirty improbable ejaculations we would each have that night. It defied the laws of biology and reason.

“I’m just cumming and cumming,” Dirk cried. “Each one is better than the last.”

It was true, if you ever get into this crazed state, you will learn this frightening truth. Just when you thought you had the greatest orgasm ever and could not possibly achieve any more pleasure, the next one will double in intensity.

“It’s exponential,” said Dirk.

And I realized he had cracked that the intensity of orgasms was logarithmic when you are being cucked.

It just gets better and better and better.


We couldn’t believe it!

Read Colt Stevens on Amazon here.

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