Cuckold Vacation

Part One

Chapter One

 

Show me your cock.

Jason stared at the message on his phone. It was the first time anyone had ever actually asked him for a dick pic. He wasn’t sure it was real. Of course, nothing he was doing with Maddie seemed real. He was reasonably certain he was being catfished and this was the culmination of all that. Someone wanted him to show them his cock to humiliate him.

That wasn’t going to happen.

He was walking to class and sexting only made that more difficult as his cock steadily grew inside his jeans. Show me your tits first. And your face.

The classroom building was just up ahead. He didn’t have much time to finish this; the professor of his DifEQ class dismissed student for using phones during class. It was too much to risk.

He didn’t expect an answer, but right as he walked through the vestibule, his phone buzzed with a message. Glancing at it, he stumbled and nearly walked into the doorframe of the second entrance. It was Maddie. Maddie topless. At least it looked like Maddie. Maybe it was photoshopped. If it was, it was a good shop. Her dark blonde hair was swept back from her face and her tits were bigger than he would have guessed.

They were spectacular as well.

“Holy fucking shit,” he breathed.

The photo came with a short message as well. Where’s my dick pic?

Glancing at the time, he still had a few minutes. He pecked out a quick message. Hard or soft?

Her answer came back frighteningly quick. Both.

He didn’t have time. There was no way around it. Class was more important.

Class was more important. School was too expensive.

His phone kept buzzing through the class. It was annoying, but silent. The professor didn’t notice. Jason didn’t dare try to turn off his phone without taking it out of his pocket and taking it out of his pocket was a nonstarter.

The class was two hours long. It was going to be annoying.

It was Jason’s lucky day. Not that math majors believed in luck, just chance distribution.

“Ten minute break,” the professor announced. “Use the time wisely to study. We’re having an unannounced quiz when we get back.” His lips twitched a little in amusement. “I’m announcing an unannounced quiz.”

The class laughed politely. Jason bolted for the bathroom. He arrived ahead of several other students and locked himself in a stall. He scrolled through all the messages from Maddie. They were all of her tits in various poses and angles. She went so far as to pinch her nipples and send multiple requests for his cock.

He was glad he was locked in the stall. Jason dropped his pants and took a couple of shots of his cock. They weren’t the best. He wasn’t a photographer, but they were decent. And he was hard. Her pictures and thinking about fucking her made him hard. He couldn’t get it to go down.

Sorry. Hard only. You’ve got me too worked up. His face wasn’t in the picture, but that would have to be good enough for Maddie

Before he left the stall, the reply came. Good boy. Want to fuck me?

He was running out of time. He was running out of time. Yes.

There was no opportunity to wait for her answer. The phone buzzed in his hand as he walked into class. Tonight? My husband doesn’t get home until late and I’m horny right now.

Jason found it impossible to focus during class. He was certain he failed the quiz.

 

It didn’t matter to Maddie that the only picture that Jason had sent her was on his hard cock. She wasn’t interested in his when he was soft. What good was a cock if it wasn’t hard? She had only asked for a picture of him soft for comparison purposes. As it was, even without much for reference, his cock looked nice and sturdy and while not huge, he was like most Ivy League schools: more than generously well-endowed.

She had been chatting with him for the past few weeks on the hookup site she preferred. It was easy for her to attract the interest of lots of guys but she was looking for a certain type and Jason hit all of her needs: nice cock, cute and borderline handsome without being obsessive about it, athletic without being a gym rat, smart, and dominant without knowing he was dominant.

Open-minded was the last check box to fill. She’d find that out soon enough.

There was another gap in time before Jason replied. This happened periodically with him because he was a student and had another life outside of hooking up with women ten years older than him. (But she still didn’t consider herself a cougar. She was something else entirely.) Still, after an hour she started to get worried. Had she inadvertently driven him off? While she had other prospects, it was a pain in the ass to go through the usual routine of all the necessary steps to find the right guy.

When her phone alerted her with the three audible notes letting her know a text from Jason had arrived, she smiled at the response. You’re married?! The shock was palpable. The fact that he had replied was a good sign. It hadn’t driven him off. He was hornier than he was smart.

Yes. Didn’t you know?

How could I possibly know, was his response.

WTF. You didn’t seem my wedding rings in the pictures? It was a question that was asking a lot of a twenty year old boy, but it might be enough to make him realize that just maybe he needed to pay attention to what he was getting himself into rather than just think with his dick.

Although thinking with his dick was an activity she also actively encouraged.

There was a bit of a delay before his next response. She had known exactly what she was doing. The wedding rings were on display with her topless pictures, but she was certain that Jason was staring at her tits, not her fingers.

Okay, but still… His response made her smile. He was still determined.

My husband and I have an understanding.

That’s crazy.

Maybe, but I married for money. I have needs and he knows that. Want to come over and fuck me?

Maddie had always had good luck trolling for college students. Their house was reasonably near the university. Hell, the development was called University Heights even though it had nothing to do with the school.

I shouldn’t.

Keith won’t be home until nine at the earliest. She attached a picture of herself. It could have been any dirty picture in the world, but she was honest and had taken it herself. A spread open pussy would just be vulgar, but by keeping her thighs together and hinting more than showing, it was sexy rather than vulgar. The little landing strip of public hair she maintained was visible through the red lace. She even tucked a finger into the top edge of the waistband to make her point.

You’re driving me crazy. It was a reasonable response.

You can either jack off or fuck me. She included her address. Jason had already told her he had a car. You have an hour and then I get out my vibrator.

 

The doorbell ran a little less than an hour later. Maddie opened the door wearing nothing but her thin robe with her matching bra and panties on underneath. There was no reason to be subtle; he had come over for only one thing and she was willing to provide it.

On first impression, she was more than satisfied with what she saw. He wore a heavy jacket that was appropriate for the winter weather. It was open and under that he wore a t-shirt professing his love for math, jeans, and boots. His sandy blonde hair was windblown. While it was impossible to tell at the moment she knew his body was lean from all the running he did. Jason claimed the only reason he made it into the school was his running scholarship, but that ended his sophomore year and he dropped out of the team. He still ran, but only for his own amusement.

“Nice,” she said, sizing him up. The winter air made her nipples contract and she knew from previous experience that they were prominently outlined. The robe and bra were thin, plus Jason was staring at her tits and not her face.

“Hi. It’s nice to meet you in person.” His eyes didn’t move from her breasts. Maddie sort of liked that. It was innocently flattering. She took pleasure in knowing she was corrupting him.

Maddie stepped back from the door and gestured him inside. “It’s cold out.”

“Yeah.”

Once inside she took his hand. “Are you ready for this?”

“For what?’

She didn’t give him a verbal answer. She had to go up on her toes to kiss him but he didn’t pull back. His lips were cold but warmed up quickly as the kiss lingered. She pressed her body against his and slipped her hands inside his jacket. His body was warm and hard.

“We shouldn’t be doing this. You’re married.”

“And yet you came over to my house to fuck me anyway,” she said. “Come to my bedroom.” Maddie tugged once on his hand and then walked away from him, heading for the stairs. She had only gotten a few step up before she heard him following. She was certain he had gotten a good look at her ass in the process.

“You’ve got a nice home,” he said, trying to keep the conversation off the subject at hand. “It’s huge.”

“Yes. My husband works all the time. I’m a bored and lonely and horny housewife. I love to spend my husband’s money. Now that we’ve gotten all of that out of the way, shall we fuck?”

She opened the door to her bedroom. The bed was huge. It was nicely decorated, expensive without being gaudy. She perched herself on the edge of the bed. There was a single step up to the bottom of the bed. That was the most over the top thing in a bedroom that Jason had ever seen.

“Shouldn’t we…shouldn’t we do it in a guest room or some other place?”

“No. You need to fuck me in my marriage bed.”

“I…I do?”

She laughed at him. “Yes. You do. Now take off your clothes.” She allowed the robe to slip off her shoulders, but she kept on her bra and panties—for the moment, at least—and kept her legs chastely together and angled away from him. Jason wasn’t going to get a free show.

Jason realized this might be his opportunity and if he blew it…well, there would always be other women. He might look back on this with regret if he got naked and fucked her, but he would definitely look back with regret if he walked away.

It was easy to toss aside his jacket and pull loose the laces to his boots. Kicking them off he pulled off his t-shirt. Maddie admired his torso; he wasn’t overly muscular, but just strong enough to let her know he was a man.

Pausing at his jean’s button, he said, “I hope I’m not going to disappoint you.”

Maddie smiled. “Believe me, compared to my husband, there’s no way you could disappoint me.”

Jason nodded and pushed down his jeans and underwear at the same time. He wasn’t wearing underwear that would in any way be considered sexy, so he sidestepped that issue. His cock was erect and Maddie had to stop herself from licking her lips when it came into view. As Jason hopped out of his jean’s long legs, she slipped down from the bed and fell to her knees in front of him.

“Is this okay?” he asked her. He didn’t know what else to say.

Maddie glanced up at Jason as she wrapped her small hand around the base of his cock. “Believe me, honey, that’s not something you need to ask when a woman gets down on her knees in front of you and does this.” She parted her lips and lowered her mouth down along his length.

As promised, he wasn’t huge, but he was more than large enough to satisfy. Years ago Maddie had learned the fundamentals of deep-throating. Jason had never had that treatment in his life.

He was more than pleased with what Maddie was doing for him.

It wasn’t that Jason hadn’t had sex with a lot of women—he hadn’t, he could count the number of his sex partners on one hand—so he wasn’t ashamed when he felt himself quickly reaching the crisis point. His cock was throbbing inside of Maddie’s mouth and it was going to feel terrific to finish there and have her swallow—

Abruptly she backed off, leaving his cock wet from her saliva and throbbing in anticipation. Since she didn’t want him to finish to an unsatisfying orgasm, she tightly pinched the base of his cock to prevent an unwanted ejaculation.

“Wha—what are you doing?” he gasped.

“It’s not time for you to cum yet,” she said firmly.

“Why…why not?”

She sighed and explained. “You came here to fuck me, not to get a blowjob.” Reaching easily and casually behind her back, she unhooked her bra and let it slip from her breasts, allowing them to swing free. Her breasts weren’t huge, but were full and round, perfectly complimenting her curvy body. What Jason didn’t know was that Maddie spent an incredible amount of time maintaining her body. She wasn’t athletic by any means, but she was determined not to have the corpulent body of her mother and aunts. Still, she could see the curves on her hips and breasts and upper arms that were perfect for men who loved a voluptuous woman, but one more pound and she’d be over the limit of attractiveness, at least in her own eyes.

Jason was mesmerized by her swinging tits. Under other circumstances the view alone would have been enough to cause him to cum, but with her hand wrapped firmly around his cock, that wasn’t going to happen.

“Are you ready?” she asked.

“For what?” he asked, his brain muddled by her nudity and her hand and what her mouth had been doing to him.

“To fuck me,” she laughed as she stood up and sauntered to the bed. Her panties were small enough to reveal the edges of her ass cheeks. They weren’t a thong, but were damn close. Jason watched the jiggle of her bottom. She casually went up the steps, rolled onto the bed, and opened a drawer that was built into the headboard. From the drawer she tossed a wrapped condom at him. “Put it on and let’s do this,” she said as she thrusted her hips into the air, caught the thin waistband of her panties in her thumbs, and yanked them down.

Jason missed catching the condom. His eyes were now on her pussy, barely revealed, but he could see the dark blonde landing strip that was a map to heaven. She twisted her hips back and forth, teasing him, not giving him a direct look at her pussy, but only hinting at it.

The amount of fumbling with the condom embarrassed Jason. To his way of thinking he should have been able to just open the packet and roll it on. He couldn’t. He was too nervous. It wasn’t easy knowing that Maddie was watching him do it. Eventually he got it on and managed to retain his erection. Going soft would have been the worst thing in the world at that point. He would have had to walk out of the house humiliated to never return.

Once it was on, his confidence returned and he approached the bed, cocksure and cock-first, with a grin on his face knowing he was going to fuck Maddie.

“Are you ready to fuck another man’s wife?” she asked him as he got on the bed with her.

It was possibly the only thing she could have said that would have deflated him if not for his eagerness. He could smell her body and he wanted, no, he needed to fuck her right then.

“Y-y-yes,” he said, ashamed he was stammering.

Maddie shook her head. “No. Not like that. I need a man with confidence. A man who will fuck me like he owns me. Like he has a right to my body. I’m already married to a cuckold, so I don’t need to be fucking another submissive wimp.”

“I’m going to fuck you and make you scream my name and forget your husband’s,” he said, bragging without the confidence he was displaying.

“That’s better,” she said, opening up her thighs and fully exposing herself to him. “Now prove it.”

Jason crawled on top of her all the while reflecting that this was the strangest sexual encounter he had ever had. Every other girl he had wound up in bed with, and that was a small number, it had always started with a date of some sort, conversation, a little drinking, a lot of making out, and then sex. This had gone from sexual conversation to sex right away.

He didn’t mind it.

Her body was different than those of the girls he had been with. There were signs of age, but that didn’t make her any less sexy. In some ways, it made her more attractive. The best part was she knew exactly what she was doing and didn’t hesitate. When he was on top of her, Maddie grabbed his cock and lifted up her legs to guide him smoothly into her pussy. He had been expecting some resistance to entering her but because he didn’t know how excited she was, it was a delightful surprise when he slid in.

“Oh god,” he burst out. Jason had no way to judge one woman’s sex from another, but he was certain this was the finest pussy he had ever had the privilege to be inside.

“Don’t you dare cum too soon!” Maddie warned him.

“Too soon?” He froze in place, too afraid to move any part of his body lest he should lose control and ejaculate.

“You need to make me cum first,” she told him.

“You should have told me that before I put my dick in you.”

She shifted position and wiggled her hips. “That’s the challenge, isn’t it?”

Propping himself up on his elbows a little higher, Jason evaluated the situation and made a couple of quick decisions. “I’m going to fuck you, but I’m not going to do it just once. I can cum four times a night.”

Her smile widened. “I’m looking forward to it. Wear my pussy out.”

That was all the encouragement Jason needed. He started fucking her the only way he knew how: fast and hard.

It was his lucky night. That’s how Maddie liked to be fucked.

Maddie was the best bed partner a twenty year old man could want. She truly enjoyed sex for sex’s sake and was a moderately good actress. She didn’t need to act with Jason even if he didn’t make her cum first. The way his body shook when he came pleased her more than she could have imagined.

“Did you…did you…did I make you cum?” he panted in her ear.

“Uh-huh,” she lied for him. “But I have a question for you.”

“What?”

“Can you do it again?”

“Uh-huh,” he promised. “Just give me a few minutes to recover. Where’s the bathroom.”

Maddie indulged him with a ten minute rest after he disposed of the condom and used the toilet. They lay next to each other in the bed, her fingers tracing the lines between the muscles on his body. He flexed for her when she asked and she giggled in delight when he did so. She wasn’t shy about teasing his cock either. Slowly, steadily his manhood rose up and she couldn’t resist any longer.

“Can I do it this time?” she asked.

“Do what?”

“Put it on you?”

Before he could reply she found another condom, opened it up, and rolled it expertly onto his cock. He watched in fascination and her lack of shame and her total enthusiasm.

When the tube of latex was in place Jason started to move on top of her, but Maddie took control of the situation, but made it seem like he was still in charge. “Can I ride you this time?” she asked.

“You want to be on top?”

“I want to make you happy,” she said as she moved to straddle his thighs. Her smile became wicked. “I need to serve you.”

“If you want,” he said, leaning back.

Maddie knew exactly what to do and as she knelt above him, she put his latex-covered cock into the entrance to her pussy and lowered herself down.

This being his second time with her Jason was more relaxed. As Maddie rolled her hips and made his cock dance inside her pussy, her reached up for her wonderful breasts, caressing them with reverence and admiring her body. “You’re a fantastic lay,” he complimented her.

“Thank you. I’ve had a lot of practice.”

“You have?” he asked innocently. “With your husband?”

She laughed at him and didn’t hold back at all. “No, silly. With other men. My husband is…um…” she paused in her rocking motions. “Keith isn’t well-endowed at all. I need to take my pleasure elsewhere.”

“You do this all the time?” Jason thought he was someone special. He was just another fuck for Maddie, for the moment at least.

“I do this with men who interest me,” she said, frowning. “Now do you want to fuck or do you want to talk?”

Jason wasn’t stupid. “Fuck,” he said.

Her motions got more vigorous. He could tell she was close and would be cumming soon because her pussy was hot on his cock and he could feel her tightening up. This was good, he realized, because with luck he could make her cum twice before he shot his second load.

It didn’t take him long to discover that she loved having her tits played with, however, she did give him a little more prompting for other things she liked.

“Spank me,” she told him between gasping breaths as he ass moved faster and faster as she chased an elusive orgasm.

“What?”

“Spank! Me! Spank my ass!”

Jason only had to be told twice. He wasn’t sure how hard to hit her, so he started off mildly.

“Harder!”

A few firm smacks later Maddie was screaming out her orgasm and Jason was proud of himself. She paused for only a minute before riding him again. “More,” she begged.

Jason indulged her. It was his pleasure to pleasure her.

The smacks he gave her were shocking to his ears, but she seemed to love it. After her second orgasm he managed to finish a second time as well.

Maddie collapsed on him, but once he had finished pumping his spunk into her pussy she whispered in his ear. “Only two more times to go. I’m going to wear you out.”

She kept her promise. It took an hour but she managed to drag two more ejaculations out of him. Jason was grateful when it was all over and he had started to put his clothes back on.

“Make me a promise?” she asked as he dressed.

“What promise?”

“After tonight, I want you to get tested and if you come up clean, I’ll fuck you bareback.”

It was an easy promise to keep. “Okay.” He was too exhausted to argue. He was almost too exhausted to walk to his car and drive back to the house he rented with his other college friends.

It didn’t occur to him to ask if she was sore or to think about her reddened ass. There was no way to hide it from her husband.

 

 

Chapter Two

 

Jason was certain he was going to be humiliated when he walked into the clinic that Maddie had recommended. Hell, it wasn’t just a recommendation, it was essentially an order. Since she had promised to pay for the testing out of her pocket, it wouldn’t go to his insurance…or rather it wouldn’t go to his parents’ insurance. He couldn’t afford to have them find out about what he was doing.

The nurses and staff at the clinic were surprisingly nice. He had a decent cover story. “Uh…I’m a student at the university and, um, I’ve had sex with a few girls. I think I better get tested.”

It was a story they had heard a thousand times before. It was also true enough story from Jason’s perspective. The nurses didn’t even blink.

It took a couple of days but when he got the results he immediately took a picture of the form declaring he was clean and texted it to Maddie.

He had expected a delay in her reply since it was late in the afternoon. To his surprise, it only took her five minutes to send back a response.

Want to come over and fuck me again?

Jason didn’t have to give it any thought. Yes!

This time getting to her house took no time at all.

Bringing the testing report seemed a little silly, but Jason brought it along anyway, just in case. Apparently Maddie was the trusting sort because she didn’t ask to see it. She greeted him at the front door wearing mom jeans and a hoodie. She looked like every other casual early thirties woman that Jason had ever seen. She also greeted him with an intense kiss that left him breathless.

“Upstairs for a fuck?” she asked.

“Isn’t that why I came over?”

The second time in her home, Jason was much more comfortable. They went right to the huge bed and lay down together kissing. It started with kissing and quickly progressed to undressing and petting. Jason felt like he was back in high school, except for the woman he was with was much more experienced than any girl he ever had back then.

“Fuck me doggy style,” she said when she was down to her black panties. His hand was down between her legs, fingering her pussy.

“Really? You want that?”

“I love to be fucked doggy,” she proclaimed.

Jason didn’t object. He had never been with anyone who wanted to be fucked that way, but he was open to new experiences. Getting into the position felt a little weird, but once she guided his bare cock into her pussy, it felt natural to hold onto her hips and fuck her like an animal.

The noises that Maddie made were very appreciative of his cocksmanship. He felt like he knew what he was doing and how to perfectly pleasure the woman who—for reasons unknown to him—had chosen him to be her lover.

The thought of the word “lover” made his stomach twinge. It twinged when he caught a glimpse of her left hand and the bright, sparkling ring she wore proclaiming she was a married woman.

While it might have given him a stomach twinge, it wasn’t enough to make him stop fucking her.

He could feel her right hand go down between her legs and rub her pussy. That was enough to make him stop.

“Am I doing something wrong?” he asked, spoiling the mood.

She looked at him over her shoulder, her shoulder length hair half swept back. “No. Keep going.”

“But your hand…”

She rubbed her clit again to emphasize her point and his question. “I need it to help me cum. I love getting fucked this way, but if this is going to be a problem, you can leave right now.”

Jason shut up and started fucking her again. Her fingers weren’t distracting and he quickly assimilated the rubbing motion she added to his thrusting. It didn’t take her very long to reach her first orgasm, which she announced to the world with a series of gasping exclamations that made him stop his thrusting again.

“Don’t stop,” she begged. “Don’t stop.”

That was an easy request to follow. She did stop rubbing her clit and pushed her hand lower which forced her head further down and her ass further up. Jason suddenly clued into so many people’s declared preference for the position they were in. Whatever was going on with the angle of her pussy was hitting him in all the right spots. Her hand eventually found his balls and squeezed firmly. He gasped at her touch.

“You like that?” she asked.

“Careful…” he begged.

“Fuck me hard and fast.” She squeezed a little harder, making him tense up. She felt the pulse from his cock. “Oh, you do like that. I’m not letting go until you cum.”

Jason’s range of movement was now restricted by her grip on his jewels, but that didn’t stop him from fucking her. His strokes were shorter, but they were faster and harder. Maddie grunted pleasantly with each impact.

Cumming while in the grip of a woman was a new experience for Jason and he was happy to have had it. She could feel the strain inside his sack and when they tightened up to his body as he came, shooting hot cum into her pussy, that was enough to push her over the edge again.

He thrusted a few more times as he came and forced her face down into the bed, all of his weight on top of her.

“That was perfect,” she told him. By necessity her hand had come away from his balls, but the sensations were still running through his body.

“Thank you.”

“I have a confession to make.”

In that moment everything seemed perfect. Jason couldn’t comprehend what confession she had to make…and then it occurred to him that while she had insisted on him being tested for STIs, he hadn’t made the same demand of her.

Still, he couldn’t help but make a joke. “You’re actually not married,” he kidded.

“Oh no. I’m married. Happily married.”

“If you’re happily married, why are you fucking me?”

She smiled even though he couldn’t see it. “I’m happily married because my husband allows me to fuck other men.” Maddie cleared her throat before continuing. “He encourages me to fuck other men.”

Her words disturbed Jason even though he already knew what she was telling him. “Yeah. I know.”

“And when you fucked me last week…I recorded it and showed him.”

“What?” Jason sat upright and looked around the room for a camera. He didn’t see one, but that meant nothing. The room was huge and a small video camera could have been hidden anywhere. Jason felt his heart thumping in his chest and that translated to his neck and his face. What was she plotting?

“And I’m recording us right now. Keith likes to watch.”

“What the fuck?” was all he could think to say.

“Well, it was for a fuck,” she said, rolling over and getting a little distance from Jason. She wasn’t truly worried about his reaction, but one never knew. “They were for our private use.”

“Our private use?” he parroted back at her.

“Mine and Keith. Well, mostly Keith. He likes to watch other guys fuck me. And luckily I like to fuck other guys.”

By this point Jason’s head was spinning. “What the fuck have I gotten myself into?” he asked himself.

“A good fuck, I hope.” Maddie’s reaction was so blasé that he realized in that moment he was in a completely different world than her and her husband…and everything else that they touched.

“I shouldn’t be doing this,” Jason muttered.

“I realize we deceived you, but let me explain. I think you’ll love it.”

“Love it?”

“Or at least get on board what Keith and I want.”

“What…what do the two of you want?”

Her smile was seductive and it made Jason’s stomach tighten up while making his cock hard. The second reaction wasn’t missed by Maddie. “I want you to be my bull. I want you to be the one to fuck me in front of my husband.”

“Why…why would you want that?” He was truly puzzled by what she was suggesting.

“Because it’s what Keith wants. I want what Keith wants.” She frowned. “Why are you suddenly so…reluctant? You were more than happy to fuck me before.”

“It’s just…weird.”

She pulled the sheets up, hiding her body from him. His dick didn’t waver. “You can either agree or you can get out. Simple choice.”