Date Night

“Don’t do that,” I said.

“Why?” she asked with a mischievous grin. “Does it bother you or something?”

She poked and prodded the front of my diaper with her foot beneath the table. Somehow she managed to find the perfect area under my pants, the part just beneath my cage where my balls were, kneading them softly with the balls of her toes, then the base of her high heels.

I glanced around the rest of the high-end restaurant, wondering if the other diners could hear the crinkling or notice what she was doing beneath the long red tablecloth.

“Yes, as a matter of fact,” I said, resolutely, “It does bother me.”

A mock sense of surprise flashed across her face. She put a dramatic hand to her mouth and gasped. “Am I hurting you?” she asked, genuinely concerned.

I shook my head with a smile. “Not…directly.” I said, my cock pressing incessantly against its tiny plastic prison.

She giggled at that, enjoying the fact that she was tormenting me, but relieved she wasn’t causing me intense physical pain.

I took the final bite of my steak, savoring the salty, buttery way it melted in my mouth, finishing it with a sip of Cabernet.

“So…” I said, searching for the right words. I’d been thinking about a way to broach the subject for most of the day. “Do you think I’ll be able to…” I cleared my throat awkwardly while she looked up quizzitively from her bite of stuffed quail, “...maybe get to, um…have sex tonight?”

She smirked, her eyes dancing in thought, she wiped her mouth delicately with her napkin as she finished chewing and shrugged.  “I dunno, do you think you’ve earned it?”

“I…I think so…” it came out more like a question. I certainly thought a romantic day of walking in the park with a picnic (and a, umm, diaper change), going to see a play, an art gallery, ice skating, and a fancy dinner definitely earned me some much needed relief.

But Erin just shrugged, “I don’t know. I mean, I kind of like you all pent up like this,” she said, “you were never this romantic, thoughtful, or considerate before you were caged.”

I sighed, knowing she was right. I cursed my former self for being such a stark contrast to my current persona. It’s hard to deny I became a much better husband once my ability to achieve daily orgasms was taken away.

“Do I need to remind you that you asked for this?” Erin said, crooking an accusatory eyebrow with a slight smirk across her painted lips as she took a sip of her own glass. She swished the wine in her mouth for a bit, savoring the taste before swallowing. “It was you who wanted to be put in chastity and diapers. I’m just playing along with what you said you wanted…”

Yes yes, I know. I was an idiot. It all sounded so much better in my head when I first proposed the idea last year, at this same time. We were at a much less romantic Valentine’s Day dinner at Buffalo Wild Wings, watching whatever hockey game was on that night. Our marriage had grown stale the last few years, so I decided to present her with some of my longtime fetishes to try and spice things up.

“I do have to hand it to you though,” Erin conceded, “This last year has probably been one of the best in our 9 years of marriage.”

There was no arguing that. I had become a much better husband ever since I was regularly ‘forced’ to wear diapers and chastity. It started small, with Erin having me clean the house in nothing but a diaper and a t-shirt. I remember sneaking in the broom closet, rubbing furiously at my crotch in an effort to get any sort of stimulation to my penis that was screaming for attention.

I didn’t have to wait long back then. I was usually unlocked after my chores were done, and given a nice little reward to boot.

But Erin quickly figured out that the longer I was denied release, the more desperate I became. Simple chores quickly became cleaning the gutters, repairing the roof, and finally getting to that porch renovation she’d previously asked me a dozen times to do. What I’d often neglected or been too lazy to complete, I was gnawing at the bit to do if it meant I could earn an orgasm after over a week of neglect. She’d always repeat the same line over and over. “Maybe, if you’re good, I’ll unlock you.”

She took another bite of quail before pushing her chair back and smiling. “That was delicious.”

I changed the subject, knowing I wasn’t going to get the answer I wanted just yet. Erin liked to drag it out as much as possible to keep my ears perked up like a dog drooling over a treat.  We reminisced about the day we met, how we might have had kids if it were an earlier point in our lives. We talked about bills, our plans for tomorrow and what our obligations were for the weekend.

“You’re going to organize the attic.” she told me definitively. Where I would usually argue and whine about having to do something, I simply nodded submissively. She glanced at the waitress walking by our table, our waitress. She was a gorgeous woman in her mid-twenties, hair pinned up, and a button-up blouse that her breasts were threatening to burst through at any moment. Erin got an insidious look on her face.

“I want you to flirt with the waitress when she gets back.”

My fork clanked. There was a lump in my throat I couldn’t seem to swallow. “I…you what?”

“You heard me.” she said simply, smiling. “Let’s see if you still got it.”

Back in the day, I did have some moves, but it was a lot harder to be suave and confident when you were sitting in a damp diaper with your wife looking on. Before I could even fully wrap my head around what Erin was proposing, the girl appeared out of nowhere.

“Will we be having any dessert tonight?” the cute waitress asked.

My hands shook so much they clattered the fork against the plate again. “We’ll uh…I…yes.” I tugged my collar, attempting to loosen my tie and give myself some air, “We’ll have the crème brûlée.”

“Okay!” The waitress smiled sweetly, pulling the pen from her pocket and scribbling on her notepad.

Erin looked at me expectantly. I started panicking, practically shouting at the waitress to stop her from walking away.

“AH! Uh..what comes on it?” I asked, flustered.

The waitress had a hint of amusement at what must have been a silly question, but she remained professional. “Nothing comes on top of it, sir, but it is a trinity cream custard with a caramelized layer of sugar across the top.

“Oh…” I said, trying to sound interested about something I was already well aware of, “How do you…caramelize the sugar?”

“We use a small blowtorch, sir,” the waitress said, maintaining her patient smile.

“Won’t that…make it taste like gas?” I was floundering and I knew it, but I tried to find an air of confidence. This was the worst attempt at flirting I’d ever done, that I’d ever seen, and I used to work at a bar and watched patrons do some very poor, very drunken, attempts. I was sweating, I shifted in my seat, then went stockstill, worried she would be able to hear the crinkling of my diaper. Was she able to smell the piss? The baby powder?

The waitress seemed a bit flustered as well, “No sir, it’s just a small butane torch that shouldn’t affect the flavor other than to give it that nice, tasty crunch.”

I nodded like I was learning something new. I had to press on, but I didn’t know what to say. “You know, they add the smell to gas…”

The waitress looked perplexed, my wife had to cover her mouth with her hands to keep from exploding with laughter.

“I…I’m sorry?” the waitress asked.

“Gas is odorless,” I continued, cringing internally, Erin was shaking with amusement. “They add the smell so that you can tell if there’s a leak…”

“That’s…that’s really interesting…” the waitress said, acting like it was the most uninteresting thing in the world. Erin nodded for me to continue.

“Could I uh…maybe get your number?” I asked with my eyes pressed closed, willing this all to be over.

The waitress looked at me, then at Erin, and back to me.

“Isn’t that your–”

“I’m gonna go to the lady’s room.” Erin said suddenly, standing up from her seat and putting her napkin down. “Sweetheart? How’s your diaper? Do you need to come with me to get it changed?”

There are few things I wanted more than to somehow make myself disappear at that very moment. The waitress’ jaw literally dropped. She involuntarily took a step back, professionalism forgotten. “I uh…I’ll have your dessert right out.”

Her and Erin both started walking the same direction, but the waitress awkwardly pivoted and headed the opposite way so as to avoid further interaction. I couldn’t help but notice she stole a glance at my bulging pants before taking the long way around to the kitchen.

******

“MMmmm” Erin moaned with a mouthful. “Isn’t this absolutely orgasmic?” she asked with a wink, swallowing the spoonful of warm crème brûlée. The waitress had avoided eye contact the entire time she used the torch to burn the crust in front of us, scampering off as soon as it was done without another word.

Erin tickled my diaper with her foot again, probably feeling bad for embarrassing me in front of the waitress. I probably embarrassed her with my incredibly poor flirting attempt.

“You were much better when you were hitting on me,” she laughed, “I’ve never seen you that flustered. Not even the time I had you buy more diapers from the drugstore.”

I smiled sheepishly, shrugging. “I guess things always came easier with you.”

“Do you still find them easy?” She asked, looking at me seriously. “Our life together, I mean.”

I thought about that for a second. Our first 8 years had been effortless, mainly because I put very little effort into anything. Even though the last year involved me doing much more work around the house and in our relationship, I was better for it. We were both better for it. I could tell it made her happy when I paid more attention to her needs and desires, and she reciprocated that with love and affection in the way I liked it: by being treated me like a dirty little diaper dumper.

“It’s always easy with you,” I smiled, “you’re my best friend, always have been, and always will be.”

I could see her heart melting through her eyes, lit up by the candles on the centerpiece. We both raised our glasses at the same time, clanking them together and finishing them off while the waitress ducked in and brought us our check.

"Okay," Erin said, "I think you earned some sex tonight."

******

We tossed and turned on the bed, making out passionately. The wine was making my head spin with lust, or perhaps it was the whole not-cumming-for-two-weeks thing.

I was on top of her, straddling her leg. She pressed her thigh into the padding of my freshly changed diaper, it made the cage push into me, and my cock was making an equal yet opposite push back. I was damn near close to bursting through the plastic prison at any moment. She must have sensed my incessant need, or was I groaning and whimpering too much.

“You need to get me ready,” she breathed.

I knew what that meant by now. I planted kisses down a trail from her neck to her breasts, her bra already flung across the room. I spent a decent amount of time sucking on one breast while gently kneading the other with my hand. In my time spent caged, I’d learned all the basic erogenous zones. I didn’t think I needed them before, as long as it was P in the V it should be good for her right?

Wrong. One of the many things I’d learned over the past year.

I kissed down to her belly button, feeling the heat radiating from between her legs, her breath becoming more labored as her desire intensified. She was soaked by the time I got to her pussy. The pheromones radiating off of her were driving me crazy. I knew that the better the job I did now, the more likely I was to have it reciprocated. I traced the tip of my tongue between her labia, tasting her juices, moving up and down, parting the lips until I found the tiny, engorged bead that was her clit. I circled it, flicked it with the tip of my tongue, paying attention to the sounds she made that told me whether I was doing it right or doing it wrong.

I never really went down on her before I got the cage. Again, I didn’t deem it necessary. But when you’re tasked with getting your wife off before you even have a chance of getting unlocked, you learn a few things.

I continued to lick the clit while I brought a finger up to insert inside. It slipped in easily. She ground her hips into it, convulsing as I curled my finger upwards and rubbed along the ribbed folds of her G-spot.

“Oh my goddd!” She moaned as I gently sucked her clit and oscillated my finger back and forth in a sort of windshield wiper movement.

I could feel her legs ripple as she rocked herself into her first orgasm. I eased up a bit, but didn’t stop going until she gave me the signal.

From beneath the sheets, I could hear the bedside drawer opening. She kept the spare key to my cage in a lockbox there. I was elated, silently listening to the telltale sound of the combination unbeknownst to me being entered, but it never came.

Instead, I felt the breeze as she lifted the sheets a bit. She grabbed the back of my head again, but this time instead of using it to shove me into her, she raised me up just enough to slip something long and slender over her pelvis.

“Now get this ready!” She sniggered.

I could feel my stomach drop. Of course when she said we would have sex tonight she meant the most common type of ‘sex’ we have nowadays: a nice good pegging.

I whimpered in protest and disappointment, but that was about all I could do before she brought my head down onto the rubber cock. She orchestrated the up and down motion for a bit, then let me take over myself. It was much more humiliating that way. With her hand there, I could justify it as I had no choice because she was in control, without her guiding me, I had to do it all myself.

I knew that the better of a job I did now, the better it would be for me later when the pegging started. She wasn’t cruel enough to make me solely rely on my saliva for lube, but she used my enthusiasm as a determining factor for how much KY she would use throughout the process.

That’s not to say she didn’t occasionally force my head down, making me take it deep, making me choke, plugging my nose while I sputtered. The same things I used to do to her back when she would give me blowjobs. Those were now a thing of the past. The only phalluses being sucked in this house was the one attached to her strapon.

When she deemed an appropriate amount of time passed, or she just grew bored, she pulled my head up.

“Hands and knees,” she said simply, “Diaper down, you know how this goes.”

I whimpered as I clambered into position, pulling the diaper down so that it nestled just below the base of my cheeks. I should have known this was coming when she taped it a little looser than usual.

The bedsprings squeaked as she got to her knees behind me. I could hear the sounds of the straps of the harness being tightened around her waist. The dildo had a smaller, 3 inch nub at the other end. Erin was able to insert that portion into herself while the other end dangled in front of her. This way we could “both get pleasure”, as she’d say.

“Oops. Almost forgot a condom!” She exclaimed. “Be a dear, would you?”

I leaned over to the bedside table, reaching in the drawer for the strand of plastic wrappers. I hadn’t gotten to use a condom in a long time, other than for, well, these types of activities. If the clerk at the drugstore only knew that I wasn’t buying them to fuck my wife, I was buying them so she could fuck me.

Erin took the package from me with a smile, then motioned with her finger for me to turn around again. The wrapper crackled louder than my diaper, she tossed it to the side before rolling the condom down the dildo. There was a pop of the cap for the lube, then the sloshy fapping of her stroking it across the latex.  It sounded like she was squeezing out a good amount. I must have done a decent job at sucking, or she was just feeling generous because it’s Valentine’s day.

I felt her coat my crack with another squirt of lube, gasping in surprise when she worked a finger into my hole.

“You like that, bitch?” She asked.

I whimpered and nodded. “Yes ma’am.” I knew no other answer would suffice. She pressed down on my spot, giving me an intense burst of stimulation. A small moan escaped my lips before I could stop it. She giggled at that.

I exhaled once she removed her two fingers, feeling them replaced by the rubber snake. It poked around between my cheeks, looking for purchase. She knew she found the hole when I let out a whimper.

“Shhh, relax…” she whispered in her motherly tone, putting one hand on my waist to comfort me. “Deep breath.”

I followed her instructions, the head of the dildo forcing its way into my hole. To her credit, she was very gentle. Slowly working it in and out by just a few centimeters, waiting for my hole to relax and allow the invader to enter.

“That okay?” She asked about halfway in.

“Yes ma’am,” I nodded, my voice doing that high and pitchy thing it does when I’m feeling submissive.

“Do you like it when I fuck your tight little hole, baby?”

I moved my head up and down, biting the pillow to keep from squealing. “Mhmm!!”

“Tell me.”

“I love it when you fuck my ass, Mommy!”

She spanked me. Once, twice, three times. Not because I answered wrongly, but just to establish dominance. I noticed my ass became much more receptive the more submissive I got. She was balls deep now, I could feel her hips pressed against my cheeks.

“You ready?” She asked.

“Yes ma’am…” I whimpered hesitantly.

She flicked on the vibration for the dildo, a slight moan escaping from her own lips. Then she began to pound me.

******

“Take it bitch! Take it!” She was driving into me, shoving me down flat onto the bed, her hips churning up and down, back and forth.

I grasped and bit the pillow. As much as it hurt, it also felt just as good. She raked back and forth against my prostate. I could feel a sticky residue on my balls inside the diaper, I must have been leaking, a lot from what it felt like.

She got back up on her knees, pulling my hips up for me to do the same, smacking my ass because it wasn’t as quick as she wanted. Another squirt of lube, another insertion, and she was right back at it.

This time she was at a different angle though, hitting my spot with every thrust.

“There.” I moaned. “Right there!”

I heard her menacing laugh. “Yea? You like that, you little slut?”

I bit my bottom lip and nodded furiously.

“Tell me.”

“Right there. Keep fucking me there Mistress!”

She laughed again, then obliged.

“You gonna cum like a little sissy?” She breathed, “squirt in your little Pampers?!”

I could feel it building. “Yes Mistress! Yes!! Please! Right there! Don’t stop!”

This was it. I was gonna get to cum! I was going to get release! Relief.

And that’s when she pulled out.

“Nooo!” I groaned pathetically, wiggling my hips and shaking, rocking back and forth, searching for the elusive dildo. I could feel the hint of rubber, but Erin kept it away from me, laughing and watching me whine desperately.

“Now you know how it feels to be on the edge, only to have it taken away.” She cackled, a nod to all the times I came too fast or was neglectful or even apathetic of whether or not she orgasmed.

I prayed she was just teasing, just wanting to watch me squirm. But when she pulled the diaper back up to my waist, I knew it was over.

She tapped me on the padded butt, indicating I should turn over and lay down.

“Awww! Don’t look so disappointed!” She cooed, “I’ll still let you fuck me.”

My heart leaped again. “Really??”

“Yep!” She smiled, releasing the straps of the harness. She slipped it off her waist, rolling the condom up and tossing it to the side. My cock was swelling in my cage again, but she didn’t go for the lockbox, she didn’t pull the key out from the chain between her breasts. Instead, she started snaking my legs through the harness of the strapon.

******

“See? You would have came at least 5 times already!” She breathed, bouncing up and down onto the dildo on top of me. It was cinched tightly over my diaper. She had been riding me so long I already pissed it twice.

Her boobs were bouncing up and down in a delayed rhythm with her body. That, in combination with her moans and the gyrations were driving me crazy.

“I wish you would let me do it with mine…” I said pitifully.

She laughed, biting her bottom lip, her eyes still rolling in the back of her head. “If you can figure out how to make your little dick vibrate like this, then maybe.” There was nothing I could say to that.

“But if you want to feel like a big stwong man in your pissy Pampers…” she said, climbing off me and getting on all fours, just like I was earlier, “Then show me what you got, big boi!”

It was almost even more humiliating, listening to my diaper crinkle and crunch with every thrust. If the vibration was just a bit stronger, I might have been able to squeeze out a release, especially with the phantom feeling of fucking something. But instead, it felt like a constant itch I was unable to scratch.

“Harder.” She instructed, “faster, right there. Don’t stop!”

I watched her rock into her 3rd or maybe 4th orgasm. I’d honestly lost count.

Once she stopped convulsing and caught her breath. She slid away from the dildo, turned around and smiled. “You really are getting better at this!”

I nodded resolutely, still not sure what to say. She giggled at my misery, climbing up to give me a passionate kiss. “Happy Valentine’s Day!” She said sincerely, breathing heavily.

It was hard to not be resentful in that moment, but I knew she was doing what I’d asked for all those months ago. It wasn’t her fault that I didn’t realize the true gravity of the reality.

She removed the harness, giving my diaper a thorough inspection. It was a bit disheveled from the antics, but nothing a quick retaping couldn’t fix.

“I think it’s dry enough to wait for tomorrow” she said, even though we both knew it was sodden and cold.

We lay back on the bed, holding each other in our arms. She nuzzled my chin, then leaned up to kiss me.

“Good night.” She said, signaling the end of the festivities.

“Good night,” I echoed, unable to keep my voice from dripping with disappointment.

She clicked the lamp off next to her, drowning the room in darkness.

Erin inched over to her side of the bed, rustled around a bit to get comfortable, then sighed, drifting off into sleep.

I lay there, wide awake, trying to get my cock to stop screaming inside the cage. All in all, I counted myself lucky. There were tons of men who would kill to be in my position, if they only knew the frustration it entailed. But I couldn’t fault her. She was embracing her dominant role swimmingly. Better than ever. I was just going to have to get used to significantly less orgasms. The days of nightly or even weekly releases was over.

The light clicked on.

“You didn’t think I was that cruel, did you?” Erin grimaced, fishing the key up from between her breasts.

I could hardly believe it as I watched her untape both sides of my diaper, opening it up, and smirking to herself as she inserted the key into the tiny lock.

The whole time I expected her to laugh and say “just kidding” as another cruel joke, but she didn’t. The lock unclasped and the front of my cage slid off easily, allowing the head of my penis to breathe fresh air for the first time in what felt like years.

“You have 60 seconds,” she said, tapping some settings on her watch.  “Do with that what you will. But after that, the cage goes back on.”

I was speechless, mouth agape. Before I could fully grasp what was happening, she clicked her watch, and the countdown started.

“Better hurry.”

THE END

Happy Valentine's Day, everyone! Yes, I know it's a stupid 'holiday', but at least try to...pamper...someone. Or yourself ;)