Weekend Services - Day 1

The knock finally came.

I had been pacing back and forth ever since he texted “omw”.

I opened the door to see him standing there in the prissy maid outfit, wig, and flawless make-up.

“Hi...” he squeaked out. Shifting his weight from side to side, eyes darting left and right nervously, head hung a little low.

I let the silence hang between us for a bit. Relishing the added bit of humiliation as he was forced to stay outside a little longer in his outfit. He had already made his way through the apartment complex, and maybe even got lost, but any more shame I could squeeze out of him was worth it.

“Come in.” I finally said. His heels clanked a little as he entered. He was shivering from the trepidation. I was nervous too, but I couldn’t show it.

“Did you wear the other things I told you to?” I asked, trying to make my voice firm and without angst.

He nodded slowly. “Y-yes...”

“Lift up your skirt.” I commanded.

His painted nails trembled as he grasped the hem of the maid’s outfit and raised the ruffles. Between his legs was a large, white, fluffy diaper that crinkled as he shifted.

“Good gurl!” I cooed. Patting him on the padded bottom. “And inside...?”

He bit his painted lip. Sighed. And nodded.

I hooked a finger into the back of the diaper and checked inside like a parent would check a toddler for poop. The base of a pink buttplug could be seen squeezed between his cheeks. The same cheeks he was spreading apart on video chat last week as he used his prissy gurl voice to beg me to let him get fucked in there.

“And last but not least...” I peeked into the front of his diaper. It was already wet, but that wasn’t what I was concerned with. No, I was more interested in the tiny steel cage that kept his little cock locked up. “And the keys?” I asked.

This was the first time he showed any sign of running. His diaper crinkled as he squirmed. Anxious. Hesitant. Reluctant as he pulled the chain around his neck, stared at the tiny keys dangling from it in despair, closed his eyes, and handed them to me.

“Good gurl,'' I smiled. It took a lot of trust to hand someone the keys to controlling your orgasms. It meant a lot to me that he trusted me that much. I gave him a playful tweak on the nipple. Remembering that he mentioned he liked that in our chats on Kik.

This was our first ever meeting and, according to him, his first time ever meeting anyone in person after chatting with them online. Well...at least, the kind of chatting two kinky, horny people do at 2am.

“On your knees.” I ordered, and he dropped without hesitation.

I looked down at him for a good while, admiring how cute he was. He really did make a pretty gurl. I stepped forward so that my crotch was inches from his face. The bulge of my cock trying to poke through my pants.

“Kiss it.” I said.

He looked up at me with those little doe eyes. As if he was honored to be given permission. He slowly leaned forward and planted kisses along the impression my throbbing cock was making under the fabric.

“You want to suck it don’t you?” I asked.

He nodded vigorously. Continuing to plant lipstick marks on my jeans.

I wanted him to suck it too. Ever since I watched how much effort he put into sucking his little rubber dildo I made him buy and plant on a wall to send me videos of him sucking for hours. According to him, he’d never sucked a real dick before. I wanted to be his first. But not yet.

“Maybe after dinner.” I said. “Get in there and make me something tasty, maid.”

He whimpered as I jerked him by the wrist and smacked his diapered bum with a ‘thud’. I watched him scurry into the kitchen and try to get his bearings. He wriggled his thighs a bit, probably adjusting his little boner inside his cage without actually touching it. Then set to going through the fridge and cabinets to find something to cook.

******

An hour later, the maid was bringing in a tray to set down in front of me and the TV I was watching. He carried two steaming plates that smelled like heaven, placing one down on the tray in front of me: Herb roasted chicken breast, mashed potatoes, and green beans.

“Looks great, slut!” And I wasn't lying, “but I don't know why you made two plates. Your dinner is right there...” I said, kicking the dog bowl on the floor. Already full to the brim with kibble.

He looked genuinely hurt. I honestly felt bad. But he told me in our chats to be cruel to him, and that seemed apparent as he dropped on all fours, holding back tears as he slowly dipped his head in the bowl and started chewing and crunching.

After we both finished our respective meals, I clanked my fork down on the plate. Satisfied. The maid scooped up my cleaned plate, and stared at the one he was denied—still full of real food—longingly. As he turned to carry the plates back to the kitchen I stopped him.

“Wait.” I said. He froze, perhaps thinking I reconsidered. “I have to pee.”

It took a minute for him to figure out why that was his responsibility. But his soft sigh betrayed that he knew what I intended for him. He backed up, plates still in each hand, and dropped on his knees in front of me. His back facing me, he bent over slightly, exposing his already wet diaper.

I leaned forward, lifting the hem of his skirt and peeling back his diaper just a tad. I pulled my dick through the zipper, still not allowing him to see it, and started pissing into the small of his back. My warmth ran down and into the back of his diaper. He hung his head in shame as I used him as my personal toilet.

When I finished, I nudged him with my boot into his now super soggy bottom so he could whimper his way into the kitchen and do the dishes.

******

30 minutes later he was back on his knees in front of me. Awaiting his next order.

“You’ve been a good little maid so far.” I praised him.

He stifled a small smirk. “Thank you, sir.” He squeaked in his pathetic sissy gurl voice.

I placed my hand on his blushing cheeks. Caressing him with my gargantuan hands like he was an obedient puppy. He twitched at first. Probably feeling a bit uncomfortable under my admittedly creepy gaze. I pressed my large thumb into his mouth. He winced at first, but started sucking obediently.

“You wanna suck something else don’t you?” I asked. Pumping my thumb in and out of his painted lips. “You want something else in your mouth don’t you?!” He nodded vigorously. Moaning softly like a hungry whore.

“Yeshhh pweeassee” he said around my thumb that he was now practically deepthroating.

“Good” I said. Sitting back. Leaving him on his knees drooling.

“Reach into your diaper and pull out your buttplug” I commanded.

His face dropped. “Sir?” He asked incredulously.

“You fucking heard me.” I growled.

He looked so defeated as he reached back into his soggy diaper, then gasped as he removed his large, 4 inch plug. Waiting for my next order that he already probably anticipated.

“You wanted something in your mouth...” I cooked. “Looks like you found something...”

He grimaced, but didn’t dare disobey as he placed the large, pink plug into his mouth and held it there. Sucking it like a wittle pink pacifier.

“Good gurl.” I said, unable to keep myself from chuckling. “Now, have you used that diaper completely?” I asked, already knowing the answer.

Even though his diaper was sagging to the floor with piss, we both knew what was missing.

He shook his head, “no shhirr...” he mumbled around the plug.

“No you haven’t.” I stated. “But you will learn to use it from my command. So when I tell you to fill that diaper, you have exactly 60 seconds to do so. Any more will result in punishment.”

I tried to sound as harsh as possible. There were certain things I didn't want to make him do or didn’t want to deal with. But part of having a slave was breaking them completely. In the end, they’d thank you for it, and probably would be getting off to it later.

I pulled out my phone. “Your timer starts...now.”

As soon as I clicked ‘start’ the maid was clanking in his heels so he could readjust to a squatting position. He immediately started grunting and groaning behind the gag. Trying to force anything he could out and into his soaking diaper.

I watched him whimper and whine as he struggled to poop himself. He was sweating as the timer continued to tick. Knowing he had a precious few seconds left.

When the clock hit passed 60 I tsk’d “hmmm, already becoming a disobedient slut...” I said, shaking my head.

He groaned and redoubled his efforts. Knowing as much as I did that the punishment would only get worse as time went on.

Finally, 47 seconds later, there was a rather pungent stench coming from his diaper.

“I did itt shurrr” he said. Hanging his head, hiding his shame behind his wig.

“What did you do?” I asked. Because you have to make them say it...

“I...went poo poo in mah diapurr” he sniffled. Though i’m not sure if it was from the humiliation or the impending punishment.

I tapped my lap. “Up you go.”

It’s funny how subs know exactly what’s coming before you even do it. How the anticipation of getting a spanking is almost as bad as getting one. Almost.

He clambered over my lap. Sobbing softly. Undoubtedly able to feel my stiff rod poking his belly.

I hiked up his skirt and squished his mushy diaper. Feeling him tense and cringe in disgust. Then slapped his exposed thighs. Hard. “That’s one. You were 47 seconds over. Watta you say we round that to an even 50?”

I started soft at first. Warming up his thighs and sneaking a rare smack against his diaper every now and then. Enjoying the dull ‘squelch’ it made. But by 10 swats I really started letting his thighs have it.

By 20 he was crying. By 30 I expected to hear the safe word. By 40 it still didn’t come even though he was flailing and blubbering as much as the plug in his mouth would allow.

After 50, I had to help him off my lap. Letting him sob and get it all out on the floor as he clutched his blistered legs.

“There there” I said. Stroking his hair with my feet. “It’ll be ok. You know it had to be done right?”

He nodded softly. Wiping his mascara stained tears away.

“I know what might cheer you up...” I said.

He looked up to see my cock, in all its glory, out and pointing straight to the ceiling.

He hesitated. Expecting another trick. But the time had come. He’d been broken. It was time to put him back together.

“Come here.” I commanded, and he did so frantically. His tears drying almost immediately.

I pulled the plug from his mouth and tossed it to the side.

My cock was rock hard and throbbing, sticking straight up in the air. He was drooling on his knees like a dumb bimbo waiting for his next instruction.

“You may begin. Slowly.” I said. Though every part of me wanted to fuck his pretty little face, I knew it was important to ease him into his first ever blowjob.

I’d forgotten how great a warm, wet mouth feels. His pretty pink lips looked adorable around the purple head of my cock. I could see him straining to slow himself down. It took everything I had to not grab the back of his head and force it down.

But he needed very little prompting. He slowly worked all 8 inches of my cock into his mouth like he’d done it for a living. He even moaned softly with his mouth full of my meat!

“Show me what you got, slut” I said, and it was like a switch went off.

Bobbing and sucking and slurping at an astounding pace. Hand cupping and caressing my balls. Other hand making a ring at the base, stroking and using the dripping drool as lube.

It couldn’t have been more than five minutes and already I was ready to cum. I wanted it to last all night, but I knew this was only the beginning. Let the little slut feel accomplished.

“Open wide.” I ordered as I pulled his head off my cock. He gasped and grinned triumphantly. Tilting his head back and allowing that lipstick-streaked mouth to gape open. There was a crinkle as he pressed his legs together. Like he was trying to contain his little caged boner.

It only took two pumps for me to start spewing sperm all over the little slut’s face. Rope after rope of hot, sticky jizz coated the hungry whore. He looked like a glazed donut by the time I was through. A couple squirts made it onto his tongue, and he held it there obediently, even keeping it there while he sucked any remaining drops from the head of my fleshy faucet.

“Did you enjoy that, slut?” I asked.

“Yesshh shurr” he said with a full mouth of spunk.

“You want to enjoy yourself another way don’t you?” I grinned, flashing the tiny keys to his cage.

“YESHH SHUrR!!” He nodded frivolously.

“Show me how much you want it.” I said. “What you would do if I unlocked you.”

Like a bitch in heat the maid immediately dropped to the floor and started humping the carpet in his wet, stinky diaper. Grinding his hips and groaning softly with my load still on his tongue and face.

“Does that feel good, gurl?” I asked.

He nodded, face turning red under the pearly jizz. I could tell it was only frustrating him. He clenched his legs to try to appease his aching balls. The cage keeping him from any type of proper stimulation.

“Stop. Swallow. And go get cleaned up. I don’t change poopy diapers.” I said firmly. “I expect you in my room in 10 minutes”

He let out a tiny frustrated pout. Then scurried off to the bathroom. I wasn’t worried about him using the toilet. I had disabled that before he came.

*******

“How’s that? Too tight?” I asked as I cinched the last rope to his ankles. He shook his head and grunted as much as the ball gag would allow. He was now tied spread-eagle, face down on the bed.

He was wearing lacy pink baby doll lingerie. The dress and skirt were mostly see-through, but even if they weren’t, it wouldn’t have done much to hide the fresh, crinkly diaper underneath.

My cock was throbbing in my pants watching him squirm helplessly. I wanted to fuck his brains out right then and there, but I needed to take my time. Prolonging the anticipation only heightened the eventual pleasure.

I grabbed a scarf and tied it around his eyes to blindfold him. He knew what was going to happen, but depriving him of that sensory experience helped plunge him further into subspace.

His breathing intensified, telling me it was working.

*Sskkk* *Sskkk* said the tapes of his diaper as I opened the back up. Leaving the diaper under his caged cock to catch any dribbles that will most likely occur.

His hips wriggled as his bare cheeks were exposed to the breeze. It was a little cold in here, but the heat radiating from our bodies kept us warm.

I sat down on the chair next to the bed. Sipping my beer silently. Admiring his rustling confusion as he wondered what I could be up to in the darkness.

The fear of the unknown can be one of the most unnerving aphrodisiacs. The anticipation mixed with suspense of what’s to come is a very powerful--and helpless-- feeling.

So I chose to bask in it. Let him sweat it out. Until finally I couldn’t take it anymore.

His breathing halted as he felt the bed descend when I got onto it. Then it started to quicken as I inched closer. I grabbed both of his ass cheeks. Kneading them playfully as I spread them open. His hole was already lubed and prepped, but I spit on it anyway. Something about it just made me feel that much more dominant and in control. Apparently it worked to make him feel vulnerable and submissive too, because he was wriggling back and forth, making the diaper underneath him crinkle in anticipation.

I let my cock rest between the groove of his crack for a minute. Admiring how he was moving up and down underneath it. Groaning in desperation.

Finally, I couldn’t take it any more. I aimed my cock into his hole and allowed him to press back into me. We both moaned in pleasure as it entered.

I slowly worked it into and out of his ass, making sure to give time for his sphincter to fully relax.

When it finally did, and he was able to take it all the way, I let him have it.

Clap, clap, clap said my hips as I started pounding him into the bedsprings. They creaked and crinkled along with his diaper. The sissy’s moans were muffled by the ballgag and pillow, but I could tell he was in pure ecstasy.

Up and down, in and out, I drove my cock into his insides. The sissy arched his back and worked hisass against me. As if begging for every inch of me.

I pulled out and watched his hole gape and wink for a second. Watched him wiggle his hips and whimper as he searched around with his ass. Groaning into his gag as if he had an itch that needed scratching.

I obliged. Slamming my cock back into him, grabbing his hips, and giving him the business. He squeaked with each thrust, and I grunted along with him.

My dick started pulsing, the head of my cock swelling as I pumped him full of my seed. Breeding him like the little bitch that he is.

We were both breathing heavily when I withdrew my cock. I looked down to inspect the open diaper beneath him. Sure enough, there was a tiny puddle of goo coming from his cage and seeping into the padding.

“You came without permission” I said, grabbing my belt. He probably didn’t have a full sissygasm, just a bit of leakage, which is probably what he was trying to explain but the gag muffled his protests. Regardless, he had to be punished for not controlling himself.

After 20 or so swats with the belt his ass was bright red by the time I taped it up in the diaper. I uncuffed him and allowed him to sit up so that he could leak both of our loads out of his holes.

“Your bed is over there” I said, pointing to the dog kennel on the floor at the foot of the bed. He whimpered a bit, but crawled in obediently. I mercifully removed his gag before shutting the door on the cage.

He could easily get out. But he wouldn’t. He was too much of an obedient slut for that. In fact, we’ll see just how obedient he can be tomorrow…

To be continued