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Losing a Bet With my Girlfriend


Guest Orange

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This is a story I wrote recently. Although it's fiction, it's based on a few true stories, so it's not really that fictitious. I hope the ladies who are into male desp/wetting find it to their liking, as I know there is not a lot of quality material available.

==

Slowly emerging from sleep, he was greeted by the familiar feeling of warm breath and soft lips against his neck. He moaned softly, noticing the familiar, flowery scent and silky touch of his girlfriend's long, dark brown hair draped over his chest. As he noticed her fingertips gently gliding across his sides, he also noticed she was fully on top of him, pinning him down. As he slowly became aware of his surroundings, he felt a gentle rocking back and forth.

She was grinding her panties on him.

It all started two days ago when they were out shopping for clothes together. They were in the men's section of the local department store when she noticed a pair of blue and green, striped cotton sports briefs. She felt a warm shiver run down her spine as her pulse increased, imagining her boyfriend wearing them under his tight jeans or walking around the house in them.

"Ohhh, these are cute." She remarked, bending her knees slightly .

"Are they?" He questioned with a smirk. "Maybe you should buy them for me."

He had a feeling she was up to no good, but he did have a fetish for underwear that rivaled his girlfriend's, and an even bigger kink for indulging her and making her panties wet. He didn't anticipate the trouble he was about to get himself into.

"Oh should I?" She grinned mischievously. "If you want them, there's a... price."

He shivered as he felt his body warm intensely.

"Price?" He asked.

She leaned in, put her hand on the side of his stomach, placed her lips near the nape of his neck, breathing warmly, and whispered in his ear "Yes. If you want them, you have to wear them for the next three days..."

"Without orgasming." She hissed in his ear.

He gasped, knowing what a tease she could be. She was hard to resist with her dark brown eyes and long, dark hair.

He was just about to blindly, arousedly accept her proposition without question when his better senses kicked in. She must have a plan and be after something. This was some sort of pervy, erotic torture she was planning for him, where failure would surely be his demise.

"What happens if I cum?" He asked.

Her hands trembling slightly, she wrapped her arms around his neck and straddled his leg in the back of the department store, grinding super slowly against his leg through her tight, medium blue designer jeans.

"Then you have to hold it."

She felt his body tense and his breathing rapidly increase. She felt warm currents running up and down her body and a warm gush soak into her tight, silky black bikini panties.

"You have to drink six beers. One every half an hour. When you're done drinking, then I will start a timer for an hour and a half. After 45 minutes, if you haven't peed your pants, we will go for a nice, slow walk outside. If you can hold it, you win and get free underwear. But if you pee in your pants..."

He gasped in her ear. Between what she was proposing and her ever increasing tempo of grinding her jeans against his leg in the back of the store, he was shakey and sweaty with arousal.

"Then you'll be my pee slave for the remainder of the week." She giggled as she coyly stared him in the eyes.

"Y-y-yes Mistresssssssss..." He groaned as he found himself semi-involuntarily agreeing to her incredibly risky proposition for him. He was just highly intoxicated by his girlfriend's smell and his own arousal.

"Sexy!" She said as she quickly grabbed the colourful, skimpy underwear off the shelf, and took it to the register to pay. "You can put these on when we get home."

"Oh, one more thing." She whispered. "When I get to make you hold it, because let's be honest, you can't last three days, I'm going to put a lock on your jeans and make you beg me, slave."

Now he was waking on the third day of their bet. Over the last two days, she had tried everything she could to make him orgasm in his new underwear. Touching them, stripping for him, grinding on his leg and kissing his neck while he sat on the couch, walking around the house in her panties, touching herself while he watched, and all while forcing him to edge. Unfortunately, he was determine to not let her win, and had been doing exceedingly well with not letting her win. Each time she had tried, it was her who had ended up frustratedly soaking her panties.

Worse, he had been teasing and griefing her constantly about losing. He was so cocky and smug about it.

She knew, much to her pleasure, that he always was more aroused doing things to her than he was if she were doing things to him. So she had even made him kiss her entire body, massage her breasts, kiss her nipples, and kiss her thighs, but nothing had worked. Not even tying his hands behind his back and grinding her soaking, black panties against his face had worked. Even when she gave him her worn panties and told him to look at them and smell them while she touched him gently through his underwear, he still wouldn't orgasm.

Instead, he just mocked her about how embarrassing it was for a girl to lose to a guy in an orgasm holding contest.

She was frustrated, sweaty, and overly aroused. She had enough of his trolling. She wanted to punish him for his hubris so badly. Normally all of her tactics would make him orgasm for her. Who was he to deny her now? She was going to make him pee his pants for being such a jerk.

He felt her grab his arms by the wrists and pin them above his head. She rocked back and forth rhythmically, straddling his hips.

She was wearing nothing but those same black, silky panties. They had been damp, with an obvious wet patch since they were at the department store the first day. But now, they were soaked with her thick, sticky, white wetness. It had stained the front of her panties, leaving them stiff, rigid, and sticking to her pussy as they had dried.

His gaze constantly wandered from her soaked little black panties, up her slender stomach, across her pert, cute B cup breasts, and to her face where he noticed she had her eyes closed as she rocked back and forth, noticeably holding her breath. She was clearly on the edge of cumming again.

The crotch of her panties had been firmly pressed against his briefs, his ever growing morning erection constrained underneath. After teasing him for days and making him edge, his briefs were soaked with precum, constantly being released, and she loved it. His underwear were damp, sticky, and he constantly smelled like boy. It did nothing to help her frustration.

Now she was grinding and grinding, feeling her clit throb as her pussy continually spasmed gently. She was gushing all over her panties, making them shimmer in the morning light. It was getting to be so much that even her inner thighs began to glisten. More importantly, it was soaking his briefs and he was finally waking.

As he realized what was going on, with his arms pinned down, feeling her soaking him with her wetness, and the sweet scent of her incredibly wet panties reaching his nostrils, he quickly became incredibly aroused and was on the verge of losing their bet.

"Noooo, stop!" He pleaded.

He struggled to free himself, but she was 6"1 with a broad shouldered, Amazonian sort of build. She had leverage on him, and was extra strong and determined from all her excess arousal. He couldn't escape.

"Shutup and cum already." She groaned.

"I think that's your panties." He quipped back.

"I hate you so much. I'm going to make you pee your pants so bad." She replied, staring him in the eyes as she felt a hot gush of wetness soak her panties and trickle down her thigh as if she had leaked pee.

His body was frozen as he struggled not to orgasm. He could barely stand it. He could smell her, and it was making him tremble. He could feel her soak his already dirty, colourful, skimpy briefs with her wetness. She was sweaty, covered in goosebumps, shivering, and frustrated. She was pinning him down and he couldn't escape. He knew he was screwed, but it was turning him on so much.

He felt the wetness gushing over him as he felt her pussy spasm and her body shake. She groaned and shivered, threw her head back, and started to moan loudly as she collapsed on top of him, grinding hard, but slowly. He felt her gush and gush all over him. as her sweaty, soft body rubbed against him.

He couldn't take it an instant longer. He felt his body spasm, and no matter how hard he held back, he started to cum. He wrapped his arms around her back and groaned softly in her ear as he lost control, soaking his briefs.

"I win. I win. I win." She giggled with exhaustion. "You're so screwed now." They both passed out.

He woke alone in bed with the smell of coffee filling the house. She had woken before him and just stepped out of the shower. Draped in a towel, with her long, dark hair cascading down her back, he watched as she dropped her towel, walked over to her dresser, and picked out a cute pair of white, silk, bikini panties that were trimmed and accented with soft lace. He watched her step into them and pull them up over her cute butt before pulling up a pair of tight fitting blue jeans and slipping a black cotton printed t-shirt over her firm breasts.

"Nice panties." He teased.

"Don't talk too much shit. Are you ready to hold it?" She smiled mischievously.

"Can I change first?" He asked, noticing his briefs were cool, clammy, and sticky from her grinding on him earlier.

She laughed. "Remember what a cocky little troll you were when you were winning? Well, now the tables have turned, and I'm going to make you suffer. I already picked out clothes for you to wear. Get dressed and let's have some coffee."

He noticed his new pair of tight, light blue jeans laying on the bed. They hugged his butt and were snug in the crotch. He knew any leaking would show, and any kind of pants peeing would be an incredibly obvious stain.

Along with his jeans was a black t-shirt, and a black belt. He noticed there was no underwear. She really was going to make him wear the same underwear while she made him hold it.

He reluctantly got dressed and walked to the kitchen. She was leaning against the stove sipping on her coffee as she checked him out. A cup of coffee and the first beer was already waiting for him.

"I figured there isn't any reason to wait." she said. "Drink up."

"But before we begin..." she pushed him up against the wall. "Put your hands up."

He did as he was told and she kneeled in front of him. She revealed a small padlock with a small key.

"No! Stop it!" He gasped as he squirmed and tried to get away.

"I told you I'm going to make you suffer. You thought you were so cool, teasing me about not being able to make you cum. Well, now you're mine. There's no way a pants pisser like you can hold six beers for an hour and a half, especially with your jeans locked." She said.

She slipped the padlock over his jeans button and snapped it shut. She tugged on it to make sure that it wouldn't come loose, and indeed, without the lock removed, undoing his jeans was impossible. They were too fitted for him to pull down. If he wanted out of them, he would have to either get the key from her, or cut them, and since they were a $200 pair of jeans, there was no chance he would cut them. It was a perfect plan.

As he groaned and squirmed in frustration, she reached into the freezer and pulled out a large bowl.

She saw his confused look, and pointed to the contents of the bowl. He looked inside and saw a small key suspended in the middle of a frozen bowl of ice. It was the key to his jeans.

"The fun thing about doing it this way is that I can't control when you'll get your key. You can't microwave it to melt the ice because it's metal. It'll take over an hour for it to melt by itself. If you try to run warm water over it to get your key, well, good luck doing that while desperate. If you try to crack the ice with something hard, well, have you ever tried to break ice? It's really, really hard, and you'll just break the bowl."

As he finished his cup of coffee, he shifted uncomfortably in his jeans. He was shaking slightly. He wasn't truly confident he could hold as much as he had to for as long as he had to. His jeans were locked and from the sounds of her ice trick, even if he did hold it, he probably wouldn't get the keys out in time to keep his jeans dry. She could be so unreasonable sometimes, especially when she was getting him back.

Worse yet, if he did pee his pants, he would have to be her pee slave for the remaining three days of the week. That means he'd have to get explicit permission to use the washroom and probably be on a timed drinking regimen. He knew she probably wouldn't let him change if he peed his pants as slave, but would instead make him drink more and hold it more, and if he made her mad, she might even make him sleep in his wet jeans.

All that, and he'd have to fulfill her arousal as she wanted, when she wanted it.

He drank his beer while they hung out in the kitchen talking about this and that, her teasing him and taunting him. After he finished his third beer he was feeling pressure in his bladder as it constantly filled. It was a cheap trick of her to force him to drink coffee too.

"What's the matter?" She asked. "There's only three more beers to drink and three more hours to hold it. Should be fine, right? Boys are great at holding it. It's always us girls who pee our pants all the time, as you like to say."

"Please don't do this to me, Mistress." He begged.

"Well, if it were up to me, I would let you pee because I don't want to see you cry. But unfortunately, your key is trapped in ice, so you'll just have to deal."

"I've always wanted a slave. You look good on your knees, with your head up my skirt. And you always brag about how good you are at it. Well, I can't deny it, so I'll just have to abuse it while it's available."

By the time he had finished his sixth and final beer, he was feeling a ton of pressure. The worst thing about it was, he knew he just finished drinking, and his bladder would keep filling rapidly. Beer was always one of the worst tortures for his bladder. It made him very desperate, very quickly, and he always found beer desperation was hard to hold.

He was also very, very buzzed. They had just woken up, and naturally, had not eaten yet. His speech was a little slurry, he was a little slower to react, his limbs felt warm and tingly, and it was even harder to ward off her tricks.

She saw him discreetly bending at the knees and shifting back and forth. She smiled.

"Okay, 45 minutes before your walk. Good luck, and take a seat." She said.

"Take a seat?" He said anxiously.

"Yeah, I'll be right back."

She returned with two long, red silk ties. He groaned, because he knew what those were for. It was not the first time she had implemented them.

"Noooooo! Please Mistress." He pleaded.

"What does it matter what you're doing while you're holding it? You may as well be tied up. Don't complain or I'll make you drink more."

He acquiesced to her demands, sitting down and placing his arms on the arm rest of the kitchen chair. She tied his right hand to the chair, looping the ties through his fingers so he was tied tighter and had less room to move. Then she tied his left in the same fashion. She sat back, grinning.

"You look cute with that lock on your jeans, all tied up." She said.

"You're sort of at my mercy now. I mean, what if I don't untie you when the timer is up? Should I save that trick for when you're my slave, or use it now? So many decisions."

"You can't really move, so you can't stop me from tickling you either. Oh mmm, I think I'll definitely save that for when you're slave."

"Must suck being trapped there like that. Even worse having to wear those briefs. You've been wearing them for so long. It must be so frustrating for you. Having to wear them after I cummed all over them. But it's fitting for a slave. You're just lucky I'm not making you wear panties... yet."

He was now at the stage of constantly squirming in his chair. He was having constant spasms and having to squirm wildly in order to be able to keep his jeans dry. He was sweaty, buzzing hard, and still listening to his girlfriend make fun of him as she watched him squirm.

"25 more minutes before our walk. You look pretty screwed." She said smugly.

"Even if you do hold it for another 25 minutes, you'll just pee in your pants as soon as we get out the front door. Boys can never hold it. Boys always pee their pants. Haha."

Having to listen to her goad him about his predicament was not only making it much harder to hold, it was also ruining his confidence that he could hold it. He was constantly trembling, with his ass and thigh muscles clenched as his beer-and-coffee-induced pee crashed against his bladder. He was acutely aware of both his underwear and jeans pressing tightly against his body. He was doing his best to not let any leak out, because he knew when he was this desperate, any leak could soak his jeans to his knees and he'd instantly lose their bet, becoming her slave.

As she was watching him drunkenly squirm while tied to his chair, she realized that he was going to pee his pants for sure. After all, she hadn't even taken the ice bowl out of the freezer yet, so even if she wanted to let him escape the remaining hour of holding, there was no way the key would unthaw fast enough.

She started to fantasize about a wet stain growing on the crotch of his jeans, shimmering in the kitchen lights. She fantasized about his frustrated moaning. She fantasized more about how she'd get to make him her slave for the next three days. She fantasized about having him go down on her whenever she was aroused. She fantasized about how weak his bladder would be after it was stressed like this. She fantasized about all the begging and groveling and feet kissing she was about to receive. It was making her so incredibly turned on. She felt her panties grow damp, warm, and sticky under her jeans, which of course made her fantasize about pressing them against his face while she wore them.

She started to massage her breasts slowly, standing in front of him.

"It's going to be fun having you call me Mistress all weekend." She moaned.

She slowly removed her shirt, exposing her soft, firm breasts. Running her hands from her neck, all the way down the front of her chest, she reached the button of her tight jeans and undid them. She slowly slid down the zipper, watching his eyes follow her fingers the entire time. Her little white silk panties being slowly revealed.

She slowly walked a few steps closer. She was now directly in front of him. She ran her hands through his hair and pulled a handful of it playfully. Breathing heavily, she reached down and slowly slid out of her jeans. His eyes were affixed to her panties. Panties had always been one of his biggest turn ons, and these ones were extremely sexy. He also noticed they were extremely wet.

Her panties were so wet that they were glistening in the light, a dark semi-circle extending from between her legs. He could see the faint outline of her pussy as they clung to her. He could also smell them from where she was standing, which made him grind against his jeans sensually as he struggled, having to constantly hold his breath, trying to hold it.

He knew those wet panties would soon be against his face. His girlfriend had a huge fetish for having him smell her panties, one rivaling her kink for pants peeing. It always made her so hot. It made him hot too, and got him in a lot of trouble.

"Just pee your pants already." She said through deep breaths. "You still have to hold it for another 15 minutes, and then there's our walk. You're going to pee your pants walking down the street if you aren't careful."

"It won't be so bad being my slave... well, maybe it will. But it won't be so bad for me."

He was so frustrated. Aroused, but extremely desperate. He knew that if he lost, she would take full advantage of him. But at the same time, he was now involuntarily leaking small spurts into his briefs as she stood in front of him in her wet panties. He could no longer totally control it, and the spasms simply never ended now. One after another he barely held on. He was going to pee his pants.

"You're going to pee your pants." She echoed his thoughts. "Just hurry up with it. Your first act of slavery is kissing my legs. We need something to do while your key unthaws anyway."

The constant leaking in his underwear had finally started to do its damage. There had been for a while a constant, small squirting being absorbed by his briefs. They were now saturated and the damage was beginning to show on his jeans. She saw it right away and began to touch her clit in small circles through her wet panties, moaning softly.

"Hotttttttttt." She moaned, soaking her fingers.

He could hear the squish, squish, squish of her touching her sensitive, soaked, quivering pussy through her expensive panties. The smell of her fresh wetness hit his nostrils, and he moaned.

It made him lose control.

His face clenched as his bladder spasmed. He doubled over at the waist, as much as his restraints would allow, and groaned helplessly as a dark, shiny stain quickly spread in the crotch of his light jeans. She watched it run up and over his hips and pool in between his clenched thighs as it poured down his legs, staining his jeans.

He peed for about five seconds, but it was so forceful and voluminous that he was soaked to his ankles, with his pants dripping on the floor.

"Nooooooo. No. No. No." He gasped frustratedly, realizing he had lost and would now be her slave.

"It's so not fair." He complained as he squirmed uncomfortably against the fabric of his wet jeans. His bladder, now somewhat relieved, was unfortunately continuing to fill, and fill quickly.

But for her, the sight of him tied up, desperately, helplessly peeing his pants while she stood there in front of him, touching her panties, sent her over the top. She quickly started to groan loudly and tremble as her fingers continued to touch, her pussy now gushing all over her panties, saturating them as her wetness spread down her innermost thighs.

When she came to her senses and opened her eyes again, she looked down at him, noticing his face still tensed in concentration and his legs squirming. She looked down to see his jeans glistening as more pee cascaded through his crotch.

"Boys are such pants pissers." She said, out of breath.

"Can you unthaw the key now, please?" He pleaded.

"Hmmm... you know, one of the dangers of peeing in your pants, having an accident, is that you'll be stuck in pee soaked jeans until you can get to a change of clothes. I think that applies even more to a slave."

"So, no. I'll start to unthaw your little key after you have... satisfied your Mistress's wishes."

The reality is, she wasn't finished at all. She had cummed so hard when he wet his pants, but it was sort of like the prelude to the real show. Now, with him as her slave, she felt strong, confident, bold, and she wanted to really get him back for picking on her.

She untied his hands from the chair and had him get up. All of the pee pooled in his jeans poured down the back of his thighs.

She led him to the bedroom, her legs quivering the entire time, nipples totally erect.

She laid a plastic cover on the bed and told him to lay down and put his wrists together in front of him. She retied the red, silk ties on his hands so that he could barely move his hands. He certainly couldn't open and close them because of the finger lacing.

She crawled on top of him, one leg on one side, and swung the other over. She planted herself on his chest, with soaking panties well exposed.

"You know what you have to do, right?" She asked.

"Shutup." He said defiantly. "I still have to pee so much."

"Get used to it. Slaves don't get to decide when they pee." She grinned. This was going to be so fun.

She crawled up his body until her thighs were above his arms. She sat with her soaking, silk panties inches away from his face.

"Can you smell them?" She asked.

"Yes. It's gross." He replied.

She laughed, knowing he was trolling her. She frequently caught him voluntarily smelling her worn panties. It made her hot, so she would often leave them in places where he was sure to find them, knowing he would smell them, and then she could punish him.

"Sucks to be you then, slave." She grinned while she leaned forward and pressed the soaked crotch of her panties against his helpless mouth.

Grinding slowly and gently, she quickly felt her blood pressure rise as sweat poured down her entire body. She had always thought grinding her wet panties on her boyfriend's face was one of the most erotic things ever. She felt his lips crawling across the fabric as they struggled to find her clit or a lip to suck.

"I'm... I'm... wetting my pants." He gasped from under her panties. His bladder had a large capacity, although he got desperate easily. The unfortunate outcome is that if he peed his pants once, he would often pee them several more times as his bladder continued to fill.

She turned around while she was grinding his face and looked at the crotch of his jeans, hearing a distinct hissing as he pissed himself.

She reached down and pulled her wet panties to the side. "Just finish wetting your pants already, slave."

He quickly slid his tongue between her lips, slowly sliding it inside as far as it would go, pointing it upwards. His lips wrapped around her clit, and he sucked gently and rhythmically. She moaned and clenched her thighs as her pussy spasmed. She looked back to see him still peeing in his pants. His jeans were soaked. She had him just where she wanted him.

Orgasm gripped her as he teased the inside, top of her pussy with the tip of his tongue and sucked on her clit. She moaned loudly, her abdomen muscles, normally smooth and fair since she was slender but didn't work out, were tensed and well defined. She gushed wetness all over his mouth as her pussy contracted against his soft tongue.

When the surge subsided, she crawled off him and collapsed on the bed next to him. Breathing heavily and obviously exhausted. She was beginning to doze off.

"Hey!" He shook her. "No sleeping. You need to unthaw my key."

"M..maybe after I wake up, slave." She said groggily, before passing out, snoring loudly.

He drunkenly, tiredly lamented against the wet fabric of his soaked jeans, his tied hands, and the lock.

"This is going to be a long three days." He thought to himself before passing out, still trapped in his pee soaked jeans.

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Oh wow, this is a truly amazing story, made my night ;p

lol, joking (ish) but this is one of the best I have seen, perhaps you could tell us more about the slavery? ;) xD

I'm glad you liked it. When we woke up, naturally I had to pee, but she wouldn't let me. Instead, she told me I had to stand in the shower and let go in my jeans. It was torturous because my jeans were mostly dry by then and I had to soak them to my ankles again. Worse was I had to start drinking on her schedule after and could only pee with her permission. I had no changes of clothes, trapped at her house, begging her to let me go. She made me go down on her when I was desperate, so I spent a lot of time having accidents while my face was between her legs.
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I'm glad you liked it. When we woke up, naturally I had to pee, but she wouldn't let me. Instead, she told me I had to stand in the shower and let go in my jeans. It was torturous because my jeans were mostly dry by then and I had to soak them to my ankles again. Worse was I had to start drinking on her schedule after and could only pee with her permission. I had no changes of clothes, trapped at her house, begging her to let me go. She made me go down on her when I was desperate, so I spent a lot of time having accidents while my face was between her legs.

Nice ;3 XD
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