He Puts on a Disguise to Tail His Wife on Her Date

A cuckold’s life is full of surprises…

“Where are you going?”

“None of your business,” the hotwife told the cuckold. “Don’t ask again or I won’t let you touch me for a month.”

“Who are you going with?”

“I told you!” she snapped. “Don’t ask that! How dare you, cuckold. Whom I go out with is my business, remember?”

“I remember,” he said, sheepishly.

His wife was getting dressed to go out. Nothing too fancy. But he surmised that it was a date, from the way she occasionally looked down at her phone, and smiled at texts. And also from the fragrance she put on. That was her hotwifing fragrance, the Givenchy. It smelled like eroticism.

“When will you be home?” he asked, as she went downstairs and got her coat.

“Hopefully not until tomorrow,” she smiled at him. “If all goes according to plan, that is.”

She gave him a little peck on the cheek.

“My Uber’s here, gotta go!”

She went out the front door.

He grabbed his disguise and headed out the back door. He had parked his rented car on the back street, so she wouldn’t notice him pulling out onto Pine Street behind her in the Uber. Yes, it cost him forty bucks to rent this car but it was worth it. He was right behind the Uber now. He was wearing a heavy beard and a wig hat that had fake dreadlocks coming out of it. He looked like a 20-something hipster, not the 40-year-old accountant who had married this beautiful woman fifteen years his junior, and was now living the life of a submissive cuck.

He knew the consequences would be very grave if she spotted him. She might put him back in the chastity cage. That thing hurt and was very inconvenient to wear to work! He’d spent a month in that thing after she spotted him at a dance club she went to with a bull. “Spying in the darkness with that pathetic look on your face,” she had scolded him. “If you ever dare do anything like that to violate my privacy, I’ll make you wear the cage for a year, do you hear me?”

“Yes dear,” he murmured, humbly.

But the thrill was just too much. He couldn’t resist any longer. He had gone to all this trouble, renting the car, buying the disguise, but at some point, he was going to get caught. He realized that. Maybe that was part of the game?

The Uber dropped his wife off in the downtown restaurant and bar district. He parked his rental car down the street and walked back past the bar that she had entered. Thankfully, she had seated herself in the front patio area and was waiting for her date to arrive. He continued past, then circled back, crossed the street and entered the little green square that sat opposite the bar patio where she sat. There he saw an enormous oak tree. It was dark in the park. He looked around. Nobody was watching him as he hopped up onto the tree, and pulled himself about halfway up, to a perfect vantage point where he could look across the street at the bar where his wife sat. He pulled out a pair of binoculars and zoomed in, holding the binoculars steady with both hands, while leaning forward against a branch to keep from falling out of the tree.

God she looked beautiful. She had long black hair. Just a touch of makeup was all her face with the high cheekbones and the symmetrical features needed. Her dress was tight but modestly cut, showing the suppleness of her figure. It fell slightly above the knee, so he could see a flash of flesh under the table, her lovely legs. She was sipping on a glass of wine. Suddenly her face brightened with a smile and she stood up. Her date had arrived. The guy gave her a quick peck on the cheek and sat down opposite her.

This was the first time they had met, he knew that. She met him on Tinder and they had been texting back and forth flirtatiously. He knew that because she intentionally left her phone around for him to sneak glances at when she wasn’t looking. She had probably taken the password protection off the phone for this very reason — so she could keep him posted, so to speak, about her affairs. She liked him to know about them, of course. Pretending she wanted her privacy was just a game that made the whole thing more fun for her.

His name was Charlie. He was super handsome. And charming and really into his wife, Beth. Charlie and Beth had been really hamming it up on the texts, with double entendres and enthusiasms that husbands and wives can’t have in conversation, of course. No, this kind of charming interaction only happens at the beginning.

If only he could hear their conversation, thought the cuckold, as he sat in his tree with his binoculars focused on his wife. He did his best to lip-read. He had even taken a crash course in lip-reading for this very purpose. He was so often watching his wife from a distance that he thought it would help to be able to discern her words from her lip movements. The course had helped a bit, but of course, often the lips are at the wrong angle. Now for instance, he could see what his wife was saying. “I’ve been so excited to finally meet you in person,” she said. But Charlie was turned at a slight angle so the cuckold couldn’t really see what he said in response.

It was something to watch his wife on a date. His chest was filled with excitement and jealousy and passion and all sorts of emotions. He felt so alive. Adrenaline flowing. He felt like a great athlete so involved in the flow of his sport that nothing else existed but he and the object of his focus — his wife and Charlie.

“Hey!” said a loud voice suddenly. “You mind telling me what the hell you’re doing up there?”

The cuckold looked down. It was a cop! Oh shit.

“Um… evening, officer. I’m just waiting. Last night there was a very rare owl in these trees. So I came back tonight with these binoculars…I’m an ornithologist, you know. A bird watcher.”

“Is that right?” said the cop. “Well, you need to come down from there. Didn’t you read the signs? You’re not allowed to climb these trees. Move along now.”

“Yes, sir,” he said. And he came down from the tree and walked away. When he looked up across the street, their table was empty — they had left!

“Shit,” he said. He hurried over toward the restaurant, and he saw them walking hand in hand about fifty yards down the street. He trailed them at a distance. They ducked into a little ice cream place. It was crowded. There was a line of about ten people waiting for some kind of fancy ice cream. He decided to risk it. He waited for a few people to go in, and then he joined the back of the line. The place had a lot of mirrors. He could see his wife’s beautiful face clearly now as she stood in line, holding hands with Charlie. He could see his features more clearly now. He looked very square, somehow, like he could be in the military or a fireman or something. That was his wife’s favorite type — a real macho man, unlike her husband, the accountant who didn’t know anything about hunting, fishing or monster trucks!

“This line is taking forever,” he could see his wife saying in the mirror. “How shall we amuse ourselves?”

“Well, we could try our first kiss,” he saw Charlie saying.

“What a good idea,” agreed his wife.

And there, only a few spaces ahead of him in line, they started making out. He thought he could even hear her sighs of pleasure as their mouths pressed together. He started getting an erection. Luckily his penis was very small so it was not likely to cause him any embarrassment in the public setting.

After the kiss, it was their turn to approach the counter. They took turns giving each other tastes from the little sample sticks. The cuckold thought he would have been annoyed if he was one of the other customers, because they tasted about twenty different flavors while they were all standing there waiting. Only the cuckold could have stood there for all time. To see that joyful expression in her eyes, as she held the stick up and put it in her new boyfriend’s mouth. So much life there.

When did her eyes become dead with me? he wondered. And were his eyes dead with her?

His eyes now were almost bulging.

They finally settled on a flavor and shared just one ice cream cone between them in the front of the store.

When he got to the front of the line the clerk was surprised to hear he didn’t want anything.

“Then why did you just wait in that long line,” the clerk wondered.

“Oh, I had my reasons,” he said. From the front of the line he could look through the glass window of the storefront at the happy couple sitting at a little wrought iron table and sharing the ice cream. In between bites they would take a break to make out some more. He watched the ice cream melt and drip to the sidewalk from his wife’s hand as she forgot about it — the taste of Charlie’s mouth was obviously more exciting to her. And now he was being bold enough to put his hands on her.

“Sir, are you just going to stand there?” asked the clerk.

“Just for a minute, do you mind?” he asked. “I just need to…catch my breath.”

The clerk shook his head. Everybody obviously thought he was crazy, with his dreadlocks and his heavy beard. Maybe they thought he was a homeless guy. He didn’t care.

Was he crazy? he wondered, as he finally left the line and followed the happy couple as they got up, and began walking hand in hand down the sidewalk. Soon they entered that same park where he had been perched with his binoculars earlier. His heart raced. There could be only one reason they would want to go in there, he thought. They wanted to move this petting to the next heavier level, and what better place than one of those benches in the dark park?

In a minute they were sitting together in a dark corner, and kissing passionately. He ducked behind a tree not thirty feet from their bench. He took out his binoculars and trained them on the couple. He saw Charlie’s hand slowly going up his wife’s skirt. He zoomed in on her face. He could lip-read her saying, “Oh yes, baby, do that, do that some more,” as Charlie fingered her. “I can’t wait to have something more than your fingers in there.”

“I can’t wait to give you something more than these fingers,” he could see Charlie saying.

“Are you very big?” she said. “Let me feel.”

He saw her put her hand on his crotch, where through his binoculars he saw a large bulge.

“Oh yes, you’re perfect,” he saw her saying. “I knew you would be. I can’t wait to make love. Let’s go back to your house and fuck all night. I want you in me, baby.”

“And your husband really doesn’t mind, huh?” he saw Charlie saying.

“My husband doesn’t matter,” he saw her saying. “He’s the least important thing in the world. He’s less important than a fly, do you understand that?”

“I think so,” Charlie said. “I just hope…I guess I just hope that one day I won’t be less important than a fly.”

“Ha,” his wife said. “You’re a real man, Charlie. That’s what I was trying to explain to you in the bar. My husband’s not like you. He lacks, I don’t know, he lacks masculine energy. He’s just so…weak and passive. It just drives me crazy!”

“You drive me crazy, baby,” Charlie said. And he saw Charlie unzip his fly and pull out an enormous hard-on. She put her hand on it and started stroking. He was hoping she would say some more stuff about how insignificant and loathsome her husband was. That, for some reason, gave him the greatest pleasure of all — even more than these pornographic moments he was witnessing. He was absolutely thrilled by it. He didn’t know why. Maybe because he was hearing her speak the truth, the truth she couldn’t say to his face but they both understood. Finally, he was hearing it, and he felt set free, elated, and authentic for the first moment in his life. He reached down and started feeling his own small dick through his pants as his wife gave this hot guy a handjob. It was quite fantastic. Until…

“You found that rare owl, by the looks of it,” said a voice.

It was the cop.

“Officer!” he said. “I, I….”

“And it is a very nice looking owl, I’ll give you that,” said the policeman, glancing over at the couple on the bench. “But unfortunately, it’s illegal to masturbate in a public park.”

“Officer,” he said. “I wasn’t masturbating. I…I…have a medical condition. I was just in a little pain there and…”

“Oh, I’ll bet you’re in pain,” said the cop. “So, let me guess. That’s your wife over there with her boyfriend.”

He looked at the cop, stunned.

“How did you know?” he said.

“You’ve got it written all over your face,” the cop said. He reached over and he removed the heavy fake beard, and pulled off the dreadlock wig cap. “Yeah,” he said. “That’s exactly what I thought.”

“What?”

“You’re a cuck,” the cop said.

“How did you know?” he asked.

“Well, it takes one to know one, bud,” said the cop. “I’ve been in the lifestyle for about three years. It’s pretty fucking awesome, eh?”

“Nothing better,” he said. “I’m glad you understand. You had me scared for a minute there.”

“I’ll tell you what,” said the cop. “Why don’t you go back to your binoculars there, and I’ll help you out a bit.”

“OK,” he said, confused.

He put the binoculars up to his eyes. Charlie was slowly pulling his wife’s panties off now. He could catch a glimpse of her pubic hair as she spread her legs and allowed him to fuck her more deeply with her fingers.

At the same time, the cuckold felt his fly being unzipped. And a hand on his erection.

Slowly, the cop began stroking his dick.

“Yeah, take a good look, cuckold,” said the cop. “That’s your sexy wife there, getting her pussy fingered by a real hot stud. He’s probably going to make her cum right there on the bench. Give her what you can’t give her. An orgasm, am I right?”

“You’re right.”

“Look at her, she’s cumming right now, isn’t she?”

“I think so,” he said. He zoomed in on her face. She looked like she was orgasming alright.

“Go ahead, let it go, cuckold. Let it all go. Enjoy it!”

And then, he ejaculated quite forcefully. He’d never had another man’s hand on his penis before. The cop knew what he was doing. Guys understand how to wank a bit better than women, he figured.

“Thank you,” he said, when he had finished and zipped himself up.

“Don’t mention it. You have a nice evening now,” said the cop.

The cop walked away. Over there on the park bench his wife was climbing onto Charlie’s lap. She was about to fuck him right there. Right there in the park. The same park where he had just gotten jerked off, by a cop no less.

A cuckold’s life! You never know what’s going to happen next!