Caleb’s wife takes his submission to the next level by forcing him to start serving her by serving men pushing their dom/sub dynamic to new boundaries. Stephanie pushes him harder than ever before, testing not just his physical limits but also his mental ones. After all, pushing boundaries and exploring new territory is what makes forbidden sex so intoxicating. Stephanie brings out a different side of Caleb with each new scene that he never knew existed. Will he be able to keep up with her demands? Or will she push him too far? You won’t want to miss this steamy gay short-story series!
New chapters are added often, so check back soon to see what Stephanie will make Caleb do next.
Chapter One – The Proposition
On the outside, Caleb and Stephanie seem to have the perfect marriage. They were high school sweethearts who got married right after graduation. They stayed in the same small town they grew up in. He works in the local factory while she works at the doctor’s office. They’ve been married for five years and are about to turn 23. Their life is a beautiful picture of what most couples hope for when they get married.
Behind closed doors, however, Stephanie has developed into quite the dominatrix. Caleb generally goes along with it; after all, her domineering personality is what attracts him to her. Caleb doesn’t mind playing the submissive role and has come to enjoy following her commands.
One night Stephanie approaches Caleb with an idea she can’t stop thinking about. Her idea is so dirty and dark that she has kept it to herself for months, unsure how Caleb will respond. But, she has to fulfill her desire, so she is ready to tell him now.
“Caleb,” she says one evening as he comes home from work. “I want to talk to you about something.”
He looks at her in confusion. She usually isn’t shy when something is on her mind, but something in the tone of her voice throws Caleb off.
“What’s going on?”
Stephanie walks over to him and sits next to him on the couch. Before he can say anything else, she grabs his arm and squeezes. “First things first,” she tells him, “Do you enjoy our sexual adventures?”
Her question throws Caleb off a bit. “Yes, of course.”
“I have been thinking a lot about something new. I get so turned on by it, and it’s gotten to the point where I can’t think of anything else.”
Caleb nods his head, still confused.
“This idea will be very dirty, and I’m not sure how you’ll feel about it. But I really want to try it out sometime soon.”
Caleb swallows nervously. It’s clear she wants to try something different, and he knows deep down he’s excited by it. However, he also has trouble believing that this is actually happening.
“What is it?” he asks while staring at the floor.
“I want to get on a Gridr and some other gay sites pretending to be you. I will pick a man for you to serve and provide you with instructions on what to do to serve him. When it is time to hook up, I will take you there and wait in the car until you are done. I will get the man to agree to take pictures and video of your session. Afterward, I will message him to see how well you did.”
She turns his head and looks deeply into his eyes. His heart races as he realizes what she is suggesting. He’s unsure how to respond. She takes a deep breath before continuing.
“You will have very little control over what happens during the actual encounter. You just need to obey him and me.”
Caleb’s face turns bright red. “Oh my God! This is a terrible idea!” He stands up. “I’m not gay. Why would you suggest something like that? You know I don’t want to do that.”
His wife is taken aback. “I can see it was a mistake to approach this as a question like you have a choice.”
“No, no, no! This is insane! This definitely pushes our boundaries.” He gets up from the couch and storms out to the garage.
Stephanie decides to give him some space to ponder her idea. She knows he will come around. He always complies, and she can’t imagine this time being different. She is confident that after he thinks about it, he will comply.
Over the next two days, Caleb can’t get the thought out of his head. The images he created in his mind cause a warm flood of invigorating energy, a sense of anticipation, and a breathless longing to serve her by serving men. At times the excitement and anticipation cause Caleb to become embarrassed. But, the embarrassment is what was turning him on. He liked humiliation and couldn’t think of anything more humiliating than serving his wife by serving the man of her choice.
Three days after Stephanie made her request, Caleb approached her.
“So, about our conversation the other night…” he began.
“Yes,” she responds.
“Well, I’m willing to go along with your idea. What do we do next?”
Stephanie’s face lit up with a big smile. Then, she excitedly starts explaining, “We start by creating profiles on Grindr and a few other hookup sites. Then, I will pick a man to start with small basic sex before moving on to more erotic kinky play.”
“OK. Let’s start,” Caleb said eagerly.
After a couple of days, Caleb’s gay profiles were complete and active. It didn’t take long before they were flooded with notifications.
Caleb is a handsome man. He has dark brown hair, is tight on the sides and tall on top. Caleb has a short chisled beard and hazel eyes and stands 5’11 with a fit body. Soft brown hair lightly covered his chest, and his seven-inch dick stood straight out over his small tight balls. Caleb’s young age of 22 also captured the attention of the men on the sites.
The headline of each profile suggested he had never been with a man, so there were no shortages of offers to be his first. The description stated he was married and wanted to explore gay sex. It also mentioned he wanted to take pictures and videos because he was into exhibitionism.
Some messages were from men wanting him to lick their assholes or suck them off. Others wanted him to fuck them in the ass. Finally, a few men offered to give him oral pleasure.
Chapter Two – The First Meet
Stephanie begins talking to one of the men who want to give Caleb oral pleasure. She finds out his name is Tim. He wants to meet Caleb at a local park to blow him in the back seat of his pickup truck later that afternoon. Tim explains his truck has darkly tinted windows so it would be discreet. He agreed to be recorded as long as he would get a copy of the video. After many emails back and forth between the two, Caleb and Stephanie drive to the park. Their Jeep has dark windows, too, so Stephanie was confident the man wouldn’t see her in the passenger seat.
The park is empty when they pull up next to Tim’s truck. Caleb and Stephanie sit in silence. Caleb is nervous, and his hands slightly tremor.
“What if I can’t get hard?” he asks.
“Caleb, get into that man’s truck and let him suck your cock,” Stephanie commanded.
Caleb gets out of the Jeep and walks to the pickup truck. The windows are so black he can’t see what the guy looks like. Just then, Tim opens the back door for Caleb. Caleb climbs into the back seat. As soon as he’s in the truck, Tim closes the door.
“This your first time getting sucked off by a man?” Tim asks as he unbuttons Caleb’s jeans and begins pulling them off.
“Yeah,” Caleb answers nervously.
Tim pulls Caleb’s jeans down past his knees and removes his shoes. He places his feet on the floorboard to help keep Caleb still. Then he reaches into Caleb’s boxer briefs and pulls out his soft cock. Caleb pulls out his phone to start recording. Tim starts playing with Caleb’s cock, until it gets erect. Within seconds, Caleb’s dick is standing at full attention.
“That’s a nice size,” Tim says.
“Yeah, I guess,” Caleb responds.
“Your dick is pretty wet already,” Tim continues.
Caleb blushes.
“I want to taste your cum,” Tim says. “I want to drink your seed. Shoot it down my throat.”
Caleb musters a grin and nods.
Tim leans forward and quickly takes Caleb’s cock in his mouth. It feels strange having another man sucking his cock, but Caleb was doing this for his wife. All he could think about was how letting this stranger suck his cock pleased his wife.
Caleb looks down at Tim. He’s nothing special to look at. Tim is in his 30s with messy blond hair, not fit but not heavy. His average-sized hands are soft and smooth. Caleb can’t believe this is happening. He’s in the backseat of a truck, in a park, getting his dick sucked by another man. Caleb tries to focus on the video, but he can’t stop staring at Tim’s lips wrapped tightly around his cock.
Caleb moans and thrashes his head back and forth as Tim swallows his dick. Caleb’s excitement builds. He can’t stop looking at Tim enjoying his cock, waiting for the moment he’ll shoot his load. Then, Tim reaches into Caleb’s boxers, pulls out his balls, and begins sucking on them. That drives Caleb crazy. He looks down and watches Tim licking and sucking his nuts. Tim sucks and slurps them as they start to swell up. His balls ache with a need for release.
Tim leans forward and wraps his lips around Caleb’s dickhead. Tim’s tongue licks Caleb’s shaft as he swallows to the base.
“Oohhhhhh,” Caleb moans as Tim’s mouth devours his dick.
“Don’t worry,” Tim says, “I’m gonna make sure you cum real good.”
Caleb is lost in a warm flood of excitement as Tim continues to suck him off. Tim uses his hand to massage Caleb’s balls as he sucks on them. Then, with Tim’s lips wrapped tightly around his shaft, Caleb’s body begins to tense up as he releases a massive load into Tim’s waiting mouth. The sensation is overwhelming, and Caleb can’t help but moan loudly. Tim sucks Caleb’s cock a little longer to get every drop of sperm.
“You good?” Tim asks.
“Yeah, where do you want me to send the video?” Caleb asks while shutting off the recording.
Tim provides his email address. Caleb puts his pants and shoes back on, sends Tim the video, and exits the truck.
Caleb returns to his Jeep, and as they pull out of the park, his wife asks how it went.
“I don’t know,” he says. “Tim, that was his name seemed to enjoy it.”
“Did you record it?” Stephanie asks.
“Yes,” Caleb replies.
“Well, when we get home, we will watch it while you fuck me,” Stephanie says in her dominatrix’s voice.
Caleb pauses for a moment before speaking. “I didn’t expect that.”
“I know you didn’t,” she laughs, “But I will enjoy it very much.”
Caleb smiles, but inside he is worried. He still isn’t sure about all of this. He wonders why his wife would want him to do such a thing. Is she trying to punish him? Or is this part of her plan?
Chapter Three – The Second Meet
A few weeks have passed since Stephanie made Caleb get his first blowjob from another man. One evening, Caleb and Stephanie are in bed together. Stephanie begins watching the video Caleb sent to Tim. Caleb sits next to her rubbing her shoulders. He doesn’t say anything as Stephanie watches the video. He can hear his moaning playing on her phone, and he feels embarrassed and ashamed.
“That was hot, wasn’t it?” Stephanie asks.
“Yeah, I guess so,” Caleb responds.
“Do you like watching?” she asks with a smirk on his face. She knows it makes him uncomfortable, but that is what turns her on.
Caleb looks at his wife and nods his head even though he wishes she’d stop playing it.
“Did it feel good to have another man sucking your cock?”
Caleb looks at his wife without any expression on his face and nods again.
“Why did you let him do it?” Stephanie asks.
“Because you told me to,” Caleb says.
“This is an important step in our journey,” Stephanie says. “It is crucial that you continue. It’s been a few weeks, so it is time to move to the next step.”
“Which is?” Caleb asks nervously.
“I want you to suck another man. And, I want him to cum all over your pretty face. Then I want him to scoop it off your face and feed it to you,” she says.
Caleb’s heart beats fast. “I don’t know if I can do that,” he says.
“You will do exactly what I tell you,” Stephanie says firmly.
Stephanie pulls out their tablet and begins logging into Caleb’s profiles on the gay hookup sites. There are a lot of notifications, and multiple men are currently online.
She clicks on one profile of a man named Jack. He is in his 40s and has brown hair, a full beard, a hairy chest, and blue eyes. Jack is 6’2, weighs 220 pounds, and has a chubby build. The pictures on the profile show him shirtless and wearing only his underwear. He has a big bulge in his shorts, showing off his thick 8-inch cock. Stephanie scrolls through Jack’s profile to see what he is into.
“He is looking for oral service,” she reads aloud.
“He’s kind of old and chubby,” Caleb says.
“How does that matter?” Stephanie asks.
“It just seems weird,” Caleb replies.
“Trust me, honey, this is going to be great,” Stephanie says. “Look at his cock. It’s huge!”
Caleb looks at the picture of Jack’s cock, and becomes intimidated by its size and thickness. He gags on the toothbrush every morning. How is he ever going to get that inside his mouth?
“Caleb, Jack says he can meet tonight. He just needs an hour to shower,” she says.
Um, OK,” Caleb says. He wasn’t expecting to have to do this tonight. Caleb feels his body start to get heavy with procrastination. He knows there is no way to delay this, so he doesn’t try to object. She is telling him to do this, and he has to comply.
Stephanie gets Jack’s address, and they jump into their Jeep and head to his house.
“When you get there, tell him you want to suck him off, ask him to cum on your face, and then feed it to you,” Stephanie commands. “Don’t clean up after you are done, I want to see his dried cum on your face.”
“Yes, ma’am,” replies Caleb.
They arrive at Jack’s house. Caleb steps out of the Jeep, and Stephanie stays behind like last time. Caleb rings the doorbell. Jack opens the door wearing nothing but a robe that accentuates his roundness. His thick chest hair is poking out, and Caleb can see the outline of his huge cock.
“Hi, I’m Caleb,” Caleb says.
“Hey, I’m Jack. Come in,” he replies.
Caleb follows Jack to the master bedroom.
“Kneel down on the floor,” says Jack.
“Here’s my phone to record me sucking you off. When you’re ready to blow, cum on my face, scoop it up and feed it to me. Keep recording until we are done,” Caleb says. Jack agrees, opens his robe, and begins recording.
Caleb stares at Jack’s big cock, which is already erect. He is nervous, but knows he needs to do this. Caleb kneels down and gets his face closer. He is so close he can smell Jack’s freshly showered cock. His face has never been this close to another man’s dick. His heart begins to race. Looking up, Caleb can see Jack’s round hair belly. His balls are shriveled up close to his body, and his thick 8-inch cock is rock hard.
Jack puts his hands on his hips, “what are you waiting for?” he asks.
Caleb reaches out and takes hold of Jack’s cock. He strokes it, and Jack moans. Jack’s cock feels so large and heavy he isn’t ready to take it in his mouth yet. Caleb looks up. “Is this OK?” he asks.
“Take it in your mouth,” Jack orders.
Caleb gets his mouth closer to Jack’s cock. Then, with his hand still holding Jack’s cock, he slowly sticks his tongue out, closes his eyes, and begins licking the tip of his penis. He tastes the saltiness of his precum. Caleb’s mouth puckers, his nose wrinkles, and his eyes close tightly at the taste of Jack’s precum.
“Oh yeah, that’s perfect,” Jack moans.
Caleb begins taking Jack’s cock further into his mouth. He can feel the weight of his thick cock on his tongue, and Jack moans louder. The taste and texture of Jack’s cock are different than any other he has ever had in his mouth. It’s thicker and heavier, and it makes his throat tingle. He can’t believe he is kneeling before another man and has his cock in his mouth. It feels humiliating. But, he knows he has to keep going because Jack is recoding.
“Lick my balls,” says Jack.
Caleb complies and begins licking Jack’s balls, swirling his tongue around them.
“Fuck, that’s good,” Jack says.
Caleb keeps licking and sucking on Jack’s balls. Then, he returns to working Jack’s cock, putting it deeper into his mouth. Jack moans louder.
“Ohhhh, Caleb! Fuck, you’re doing a good job!” Jack exclaims. “Are you sure this is your first time sucking a guy off?”
“Yes, sir,” replies Caleb.
“I’ve got to warn you, I’m a heavy summer, so it’s gonna be really messy and will probably cover your face and run down your neck,” Jack warns.
“That’s fine, sir. I want to be covered in your cum. The messier, the better,” says Caleb.
Caleb continues to work Jack’s cock in his mouth, frequently gaging from its massive size. He can feel his throat stretching wider as he deep throats Jack. Then, as his jaw becomes tired, Caleb stops, and Jack’s big cock slips out of his mouth. He looks up at Jack. He is smiling behind his phone while recording Caleb servicing this cock.
“Why did you stop?” asks Jack.
“My jaw hurts,” Caleb says.
“Keep going! I’m getting close.” Jack says.
Caleb continues to service Jack’s cock as best he can. He can feel Jack’s cock pulsing in his hand. Jack begins thrusting his cock into Caleb’s mouth. Caleb is no longer controlling the situation. Jack pushes his cock in deeper, causing Caleb to gag and his eyes to water. He just kneels there and takes it without trying to stop Jack.
“Caleb, I’m gonna cum,” Jack says.
Jack pulls his cock out of Caleb’s mouth just as he blasts a huge load of cum on Caleb’s face. A blob of cum hits his eyes, causing him to jerk back a little and close his eyes. He can feel the warm cum smacking him in the face and dripping down his jaw and neck. Jack wasn’t lying. His load was massive. Stream after stream of cum continues to hit Caleb’s face. Soon, it begins to drip onto Caleb’s shirt. Jack moans loudly as every drop of cum exits his cock.
Jack continues pointing the camera down, lowers his hand to Caleb’s face, takes a big scoop of cum onto his finger then forces it into Caleb’s mouth. Since his eyes were shut, Caleb wasn’t expecting it. He tries to swallow, but some of the cum dribbles out of his mouth and lands on Jack’s hand. His cum is thick, he rolls it around his tongue before swallowing. Jack laughs as he continues scoping his cum from Caleb’s face and feeding it to him. He brushes some cum off Caleb’s chin and into his mouth.
“Good boy, eat all my cum,” says Jack as he continues feeding Caleb.
After Jack feeds Caleb his cum, he asks if Caleb wants a towel to clean up.
“No, I’m good,” Caleb replies.
Jack shuts off the camera and hands Caleb his phone. Caleb asks Jack if he wants a copy of the video, to which Jack says yes and provides him with his email address. Caleb sends the video file over to Jack as promised.
Jack walks Caleb to the door and thanks him for the blowjob. Caleb gets into his Jeep and begins driving home. Stephanie could see wet spots left by Jack’s cum on Caleb’s shirt and noticed the white flakes of dried cum on his face. She began to smile.
“How was that, Caleb?” she asks.
“It was awful, ma’am,” he replies.
“You have a lot of wet spots on your shirt and dried cum on your face. It looks like he was a heavy cummer,” Stephanie remarked.
“Yes, ma’am, he was,” Caleb said.
Stephanie smiles. “Did you enjoy having your face covered in cum?”
“No, ma’am,” Caleb replied.
Stephanie grins. “Did you like him feeding you his cum?”
“No, ma’am, it was gross,” Caleb replied.
“Then why did you do it?” she asked.
“Because you told me to, ma’am,” he replied.
Stephanie grinned in response.
Caleb and Stephanie continued the drive home in silence. Once they were home, Stephanie asked Caleb for his cum soaked shirt. He handed the shirt to her. Next, she instructed him to get naked and lay on the bed.
She pushed the cum soaked shirt into Caleb’s mouth. “Suck his cum off your shirt while I give you a blow job,” she commanded.
Caleb began sucking the still wet cum off his shirt. He was tasking Jack all over again, he was humiliated. Stephanie put her lips around his cock and started sucking him off until he came. Finally, after a long night, they turned off the lights and went to bed.