Picturing Her Night Out-1

DISCLAIMER: Nothing in this story is real or should be considered as such. This story contains elements of cheating, cuckolding, sph and yes, also features sexual acts between consenting adults. I welcome any feedback and I’m always excited to discuss the story and characters, and chatting/bouncing around ideas for future stories. I hope you enjoy delving into my insane mind.

NOTE: This story focuses very heavily on themes of cheating and cuckolding and involves some extreme dirty talk and humiliation, notably of the small penis variety. This story is also much meaner compared to my usual fare, but everyone (more or less) ends up happy in the end. It will not be for everyone but I hope those that it is for enjoy it very much and find some delightfully perverted and smutty material within.


Brad’s phone buzzed beside him, the screen lighting up to reveal the image of his smiling wife. The anxious husband stopped pretending to watch tv and snatched the device from off the armrest. It had been over an hour and a half since his last message, twice as long since his first. In all that time, Betsy hadn’t replied to a single text. Yes, she was on vacation, and yes, her best friend and her husband were taking her out that night, but it was extremely unlike his wife not to respond to him, and he was getting pretty worried.

Reading her long-awaited reply didn’t lessen that concern.

You text a lot.

A prickling sensation needled at the back of his mind, the hairs on the back of his neck rising. He shifted uncomfortably in his chair. Something seemed off. Betsy never talked to him like that. She never really spoke to anyone like that. She was your typical southerner: kind and sweet to a fault, passive aggressive at her worst. Yet this message read less passive and more outright hostile. Maybe she was testing him; her bff having gotten into her head after only a few days without him around. The risk of the possibility was a big reason he hadn’t approved of this trip to begin with. Leaving Betsy alone with Trish and Dale was dangerous for his marriage.

Sorry, he wrote back. I just hadn’t heard from you was all.

This is Trish by the way. Betsy didn’t have a bag to match her new dress so I’m carrying all her stuff.

That certainly explained a bit. The unfriendly message fit Trish perfectly, especially when it came to him. Betsy’s bestie loved throwing jabs his way. Rather than fight back, however, he simply chose to try and dodge.

She bought a new dress?

We bought it for her, Trish wrote. She’d never buy something like this. But we needed something good for the club tonight.

The club? The idea of Betsy at a club seemed completely foreign to Brad. He attempted to picture his wife in that setting, standing around in a dimly lit and crowded space dressed in her usual attire of a blouse, blue jeans, and cardigan. The music thumped and blared. The ice in her glass of diet coke slowly melted. He almost laughed. He had a much easier time envisioning her at a church dinner, chatting with their neighbor Charlene and carrying their three-year-old on her arm while their five-year-old pestered her.

However, Betsy was a total pushover. If Trish insisted that she go to a club with her and Dale, she would — and would feel obligated to wear a dress if they paid for it.

What sort of dress?

One not for you.

Brad frowned. He was about to respond when the three dots reappeared.

Hang on. I took a picture of her in it earlier.

He sat up in his seat as his blue eyes bugged out of his head.

Brad had seen his wife in dresses before but those were more elegant or summery. They were nothing like this. Nothing so… overtly sexy.

After two kids, Betsy wasn’t near the slim and tight girl he first met in high school, but the style of the dress gave her extra pounds an undeniable appeal. The straps were thin chains connecting to a draped collar that exposed a touch of cleavage, and the ruched fabric outlined every bit of her curves in the most eye-catching way. Her heavier boobs appeared rounder on her ribcage. The folds of cloth de-emphasized her softer midsection but called attention to her big hips. And it drew the most tantalizing line down to her thick thighs.

His cock instantly reacted to the arousing image, growing stiff in his pants.

At a loss for words, he finally replied with a simple, Wow.

I know, right? There’s a few more from throughout the night. I guess I can send them. But you have to say please.

Brad scoffed at the suggestion. Asking for pictures of his own wife? It was ludicrous. Why would he debase himself for a photo when he could have the real deal in three days’ time and have her wear the dress for him when she returned home. Trish, however, had already seemed to anticipate that work around.

It’s the only way you’re going to get to see her in it, she texted. I told her she had to leave it here and could only wear it when she visited us. Alone. So, what’s it gonna be?

Brad scrolled back up to the picture he already had. Betsy looked so hot in it, and it’d probably be enough to get him off tonight. But the thought of seeing more was a little too much to pass up — even if Trish was intentionally pushing his buttons. He reached down and rubbed the tip of his dick from over his shorts. Or maybe it was because she was. He hated to admit it, but he enjoyed it when Trish fucked with him. She was such a bitch, but her little digs turned him on more than they pissed him off. His dick jumped every time he caught her rolling her eyes at him or making an offhanded comment about his appearance.

Fine. Can I please see more pictures of my wife?

Ugh. Don’t remind me that she married you. Another picture came in. Betsy stood facing the mirror, a strand of her summer blonde hair wrapped around a curling iron. The view from behind led his eyes right to his wife’s sizable rear. Although Betsy’s butt veered on the flatter side, the way the dress contoured to her large hips and thighs gave the wide expanse an appealing silhouette. He continued to rub at his stiff cock and zoomed in closer until his wife’s big ass took up the screen. If you want more, you’re going to have to keep asking.

Between his arousal and the pleasurable sensations of his cock tip against the fabric of his underwear, asking Betsy’s best friend for sexy pictures of his wife had shifted from absurd to kinky. Can I please see another picture of my wife?

WHAT did I tell you? Trish replied. Ask again.

Brad could hear Trish’s snarky and assertive tone across the screen, and it sent a shiver through his shaft. His wife wasn’t the only one that was a pushover. Brad secretly loved being bossed and ordered around, particularly when it came to threading this kind of sexual line. He always imagined Trish as an aggressive and dominating lover, and the idea of her ordering him around and taking control in twisted ways had crept into his fantasies. But it was never just her. His wife also played a central role in these kinky thoughts.

Betsy never acted unpleasantly toward him, but her pliability had allowed for little moments where Trish’s criticisms seeped through. Small, what-would-have-otherwise-been unmemorable occurrences that stuck in his mind because of how his prick reacted to them. His wife was normally so docile and kind that seeing her act maliciously — especially in regards to him — made for a perversely wicked contrast to the woman he knew. It led to dark fantasies of Trish manipulating Betsy and having her insult and degrade him.

Can I please see another picture of Betsy?

Two more pictures showed up. The first was a selfie of Betsy and Trish taken at the traditional downward angle. The two girls looked stunning. Unlike her friend, Trish retained a fit figure, having never had kids, only recently gotten married, and spending quite a bit of time in the gym. Although Trish’s dress showed off her shoulders and toned arms, from what was visible in the photo, it seemed much more conservative than Betsy’s. It was quite a contrast seeing his reserved wife as the more provocative of the two. A fact further emphasized in the second picture, which showed Betsy bending over and slipping on her heels. The view gave the barest glimpse down the front of her dress, and it occurred to him in that moment that she wasn’t wearing a bra.

She looks really good, doesn’t she?

She really does, he texted back. Really hot.

More than you deserve. Brad groaned. Sticky precum had formed a wet patch in his shorts. Heading into the bedroom, he slipped off his moist clothes and laid down on the mattress. He slowly pumped his cock with his fingers and read Trish’s last message. Right?


Good boy.

“Fuck,” he grunted, his eyes taking in the new images.

Betsy stood at the bar, head tossed back and taking a shot. Her long hair cascaded down her back in waves, and the slight arch of her spine pushed her boobs and butt out.

In the second picture, she sat on a stool with a cocktail in hand, and the shortness of her dress left almost all of her lower limbs exposed. Her already thick thighs appeared even bigger with one leg crossed over the other.

The final two photos were of her back up again, chatting with some guy. One had her smiling kindly, her posture straight and body leaning back as she sipped from a glass. The other looked like it was taken later: her dress a little less neat and tidy, her hair less pristine. She also seemed less stable on her feet, mid-sway. Her head was bowed slightly, and she sucked from the mixing straw of a fourth drink, her caramel eyes turned up to the guy in front of her.

Was Betsy drinking? Out of everything, that seemed like the most unbelievable aspect of all this. His wife never drank, except for special occasions like anniversaries or New Years, and even then, it was usually one glass of champagne at most. The drunkest she’d ever gotten was at Trish’s wedding and that was because Trish kept insisting her bridesmaids do shots with her.

Brad barely saw or hung out with Betsy most of the event — Trish wanted the bridesmaid and groomsmen always together — but back at the hotel, she had stumbled in drunk and horny and fucked him while still in her dress. It was one of the hottest nights of their marriage, even though — or maybe because — she kept wishing he could go deeper and criticized his lack of prowess.

Uh-huh. We did a shot when we arrived, but then this guy kept buying her drinks all night.

Which guy?

This guy.

Brad’s breath caught in his throat. A picture of Betsy on the dance floor with the same guy she’d been talking to in the previous photos popped up. He was tall and muscular with dark hair and swarthy skin. There was about a foot of distance between them, but he was clearly eyeing her up as she laughed and moved her arms to the beat. It all appeared very chaste but something about his wife dressed that way with another guy sent more pulses of pleasure through his shaft. But the two images that followed soon after that one turned up the voltage on the pleasure meter.

The one she was dancing with all night.

Betsy and the stranger clasped hands, a bit closer together as he tried to teach her how to move a bit better to the beat.

His hand on her waist and hers on his shoulder, their hips both angled toward to each other. She was still smiling at him but there was less pure amusement and more of an added touch of intensity.

She was dancing with this guy all night?

Oh yes. She really got into it. Want to see?

Brad swallowed deeply. His eyes drifted back to the last image. Yes. Please.

He waited for the next photo, his two fingers and thumb jerking at his cock. Instead, another message appeared, and it made him moan in perverse decadence.

Say please send me more pictures of my wife dancing with another guy.

I thought you didn’t want me reminding you we’re married.

I do in this case.

Please send me more pictures of my wife dancing with another guy.

Brad’s movements on his dick gathered speed. The first photo saw both the stranger’s hands holding tight to Betsy’s hips, the space between them shrinking. The second closed the gap even more, Betsy’s palm on his chest, their eyes locked onto each other.

What do you think?

Oh my god, he typed out with one hand. She looks incredible.

THEY look incredible, Trish corrected. Go ahead and admit it. Admit how hot your wife looks dancing with another guy.

Arousal overtook every emotion in Brad’s head, smothering any sense of jealousy or confusion. Trish’s depraved demands, the power she was wielding over him, seeing his wife acting so unlike herself with a random guy that was feeding her drinks… it clouded his judgment and reasoning. Submitting to Trish became the right and only course of action. And by far the hottest.

My wife looks so hot dancing with another guy.

Betsy and the stranger’s bodies met, stomachs touching, her legs on either side of one of his, a brown hand on her lower back pulling her closer.

Now, she’s never as hot as this with you.

Trish kept ordering; Brad kept obeying; and more pictures rolled in of his wife surrendering to the touch of this tan-skinned seductor.

She’s never this hot with me.

Betsy’s back against his chest and her ass covering his hips; one of his hands around her waist, right under her boobs, and the other lower on her belly, right above her panty line.

They look much better together than we do.

Dress bunched up almost to the tops of her thighs, one of his hands creeping further around her hips, fingers pressing into the cheek of her wide rear.

She deserves someone hot and not an overweight loser like me.

The two of them back at the bar, sweaty and disheveled. Betsy leaning forward and waiting for the bartender, her lips slightly parted. The guy hugged against her from behind, his arms around her waist, where exactly his hands landed obscured by the darkness under the bar.

Our kids would look cuter if she had them with someone like him.

Betsy and the guy in a similar position but back on the dance floor. Her head was against his collarbone. One of his hands snaked around her body and cupped a low breast through her dress; her hand behind her back, disappearing between their bodies.

Panting with his cock and fingers covered in a slick sheen of precum, Brad waited for the next humiliating statement Trish wanted him to say. He couldn’t believe half the things that she had gotten him to repeat, especially the last one. That one was notably fucked up, but it was close to something he had heard her say to Betsy before, that she would have found their kids cuter if she had them with someone other than him. By all rights, Betsy should have been disgusted by that, kicked Trish out of the house and never talk to her again. Instead, she just lightly and unenthusiastically scolded her. Trish had taken that as a victory.

If she had known that Brad had overheard her and later jacked off imagining her making Betsy repeat it to his face, she would have thrown a party in celebration.

He waited, but no further messages came in. Maybe she wanted him to come up with something on his own and take the initiative. She’d probably enjoy hearing him demean himself and their marriage without urging. She never should have married me, he texted.

A few agonizing seconds later, the three dots appeared.

You’re right. She shouldn’t have. She should be taking home guys like him instead of settling for your pathetic dick.

“Oh god,” Brad groaned, feeling his orgasm approaching. My wife should be out fucking hot guys like him not raising kids with me.

I’m glad you agree.

Again, nothing showed up. Aren’t you going to send another picture?

Sorry. I don’t have anymore. That was the last one.

He swore in frustration, his cock letting out a pang of disappointment. All he needed was one more picture, one more image. Can’t you take another one? Just of her in the dress.

Those were all from a while ago. She isn’t wearing it anymore. We’re back home.

That gave Brad pause. If they were home, why was he still talking to Trish instead of his wife. You are? Then can I talk to Betsy?

She’s busy, Trish said. She’s in the guest room sucking that guy off.

Brad’s hand came to a screeching halt. That had to have been a joke. That had to have been Trish fucking with him. There was no way his wife would do something like that. Regardless of the cheating, he couldn’t imagine Betsy sleeping with someone she just met hours ago. That was nothing like her. Then again, he also couldn’t have imagined her going to a club, her drinking so much, her dancing so scandalously. The other thing he couldn’t have imagined was his reaction. Instead of ruining his erection, the sudden possibility of Trish telling the truth strengthened it.

No, she’s not. You’re lying to mess with me.

Three dots appeared. Not the ones letting you know someone was typing but an ellipsis. That was Trish’s response to his disbelief.

When she didn’t elaborate further, he started to type out another message but then a new image appeared and a jet of precum shot out of his tip and splashed onto his pudgy stomach. A naked man with brown skin sat on the edge of a bed, his hands bracing on the mattress behind him. The angle of the picture put his back and thighs mostly in frame but there bent over his lap was a head of summery blonde locks.

Brad frantically zoomed in. His heart pounded in his chest. The details were hard to make out, and only the girl’s hair and a bit of her face was visible. It could be the same guy. It could be his wife. But he wasn’t certain. Maybe that was what Trish was going for. That’s not proof. That could be anyone. I still don’t believe you.

Jesus Christ. Okay, fine. How about this then. Send me a picture of your cock. I know it’s out. I know you’ve been jerking off to Betsy and that guy this whole time. Send me a picture of it and say you have a tiny dick and I’ll give you your proof.

It took a lot of effort for Brad not to cum as he snapped a photo of his hard and wet prick, typed out, I have a really small and pathetic dick, and hit send. He watched the photo upload, the sad state of his gut making the three-and-a-half-inch member appear even more pitiful.

Fuck you are small, Trish texted with a laughing face emoji. Betsy told me you were when you started dating but my god. You’re even smaller than she said. Ugh. Hang on.

Brad laid there and let his mind wander, hoping to ease his aching prick so he didn’t instantly erupt when the evidence arrived. The knowledge that his wife lied about his dick size, still acknowledging his diminutiveness but obviously embarrassed about how miniscule it really was, flipped his stomach and churned his nuts. When a video came in, he was glad he took the moment because if he hadn’t, the bed would have been covered in his seed.

It started in first-person with Trish walking toward a cracked open door. She pushed it open and sauntered into what appeared to be the guest room. First, she focused the camera on the floor, where the familiar dress lay crumbled in a pile along with a pair of pink panties. Then, she turned the lens upward, bringing into view his wife sitting on her haunches, her head bobbing up and down the guy’s lap. The view was from the back, but the deliciously wet sucking sounds confirmed she was in the middle of blowing him.

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