Worlds First Futa - Sissy Maid

I thrust my hips forward and let my cock sink inside. It was heavenly. His ass was tight, hot, squeezing all around me and felt like it was sucking me in. Thanks to all the foreplay, half of me slid smoothly into him with no effort. I could feel his prostate getting crushed to a pulp under my thick shaft.

Jamie screamed out in pleasure.

"Oh my goooddd yeesssss!"

"You feel soooo good Mistress. It's happening, I can feeeel it. I'm going to cuuuuum."

His asshole clamped down hard around my shaft and his hips bucked. Once, twice, three times. I couldn't see, but I knew that each time his sissy clit had squirted onto the bed beneath him. When he finished, his whole body went soft as his muscles relaxed and I slid another couple of inches deeper.

"Such a good girl, cumming without ever touching your cock!"

"How was your first sissygasm sweetie?"

"Amazing."

At least I think that's what he said, his face was muffled by the pillow.

"Good, because that's the only way you're ever going to cum again."

"I'm going to really fuck you now pet, you can cum as many times as you want."

I pulled my hips back and slammed forward. He was lubed up and my cock was leaking pre-cum like crazy so the journey to the deepest part of him was smooth. After a few minutes of steady thrusting, my hips came to rest against his cheeks.

I flexed my kegel muscles so my cock twitched inside of him.

"How does that feel sissy? Fourteen inches of fat futa cock stuffed up your ass."

The only response I got from him was a gurgle and his hands coming back between his legs to fondle my balls.

"I guess that means you want me to fill you up with cum huh?"

"Very well, but don't blame me if you can't live without the feeling of me breeding you."

I pulled back so just the tip remained then slammed in hard. I started slow at first, but steadily increased my tempo. I didn't take me long to get up to full speed, driving every inch of my cock deep into him. The feeling was sublime.

After some time, I adjusted my position. When I pulled out I could see his gaping hole twitching as it desperately tried to be filled once more. There was a large puddle of thin cum pooled between his knees. Jamie must have cum at least 3 times. Now it was my turn.

I raised myself to my feet and squatted over ass. I pulled his knees into his chest and pushed his back down so it arched strongly and pushed his ass upwards. I slid my length back into him and got a good grip round his waist for balance. In this stance I would be able to drive my hips downward with a lot of power.

Once ready, I lifted up and did just that, the head of my cock punching deep into his guts. I found my rhythm again and knew that this time I wouldn't be able to stop until I had completely filled him with my seed.

I was like a fucking machine, becoming utterly relentless. Jamie moaned and shook and whimpered as he came another 3 or 4 times. Every thrust sent my cock slamming deep into him and my balls slapping hard against his.

I don't know how long this went on for. It must have sounded like a sexual metronome.

Plap. Plap. Plap. Plap. Plap. Plap. Plap.

When I finally came, it was a monster load. I sank my cock deep into him and held it there as innumerable blasts of hot, sticky jizz filled his bowels to bursting.

I sighed contentedly and pulled out. His hole was a ruined mess that didn't look like it was going to close up again any time soon. Thick streams of my cum bubbled out of it and streamed down over his caged dick and down his legs. He was clutching his bloated belly and moaning loudly, lost somewhere in the pain and pleasure.

I wiped off the mess of cum left on my cock with his pillow then kissed him softly on the forehead.

"You were a very good girl tonight Jamie. Sweet dreams. Don't forget about my morning blowjob."

-

Now that Jamie had submitted fully to me it was time for his advanced training. He had accepted his place and embraced the life of a sissy. I was going to make him the hottest, sluttiest, most depraved sissy he could be.

The very next day I took every single item of male clothing he had left, and any of his possessions I considered to be masculine and donated the lot to charity. He would be a sissy girl at all times now. He didn't seem to mind. I don't think I'd even seem him wear any of those clothes in weeks anyway.

Since my guest room needed redecorating, I set myself to the task of turning it simultaneously into a pink, girly paradise and all purpose fuck den.

I took out all the existing furniture and painted the walls a light pastel pink then fitted a white carpet. I hung flowery curtains and bought a desk, wardrobe and chest of drawers. All of them were also pink. The most extravagant purchase was a large 4 poster bed, that I also decorated pink and hung with transparent, veil like curtains. The bed had a few extras, including an adjustable angle mattress, various attachment points on the pillars and headboard and a central bracket for a heavy mount like a sex swing. It was also surprisingly comfortable for sleeping on.

My favorite touch was the special messages I left for him on the walls. You know how you can order wall writing in pretty script? It's usually banal tripe like 'Live, Laugh, Love'.

Instead I ordered a DIY stencil set and painted him some more appropriate messages for his new position.

'Sissy Fucktoy'

'Slave to Futa Cock'

'Obey your Mistress'

You get the idea.

I upgraded his uniform too. I bought an even more over sexualised, fetish version of the french maid outfit. The skirt was so short it hung off his bubble butt leaving his cheeks bare and his buttplug on display. Round the front it just barely covered his cage. I changed his footwear to 5 inch black heels that came with a locking mechanism around his ankles. Sometimes I would even make him sleep whilst wearing them.

To go along with all this, I increased and furthered his training. I ordered him to spend his most of his free time watching sissy hypnosis videos through a VR headset whilst playing with his ass or sucking on a dildo. I also installed speakers in his room to play subliminal messaging during the night. My favorite track was a hypnotic loop entitled 'You Yearn for Cum'. His morning blowjob was always particularly voracious after he listened to that all night.

I kept him wearing a buttplug at all times except for cleaning, and I purchased him one that I could remotely control the vibrations of via my phone. I usually left it on minimum speed throughout the day but would occasionally spike it up to maximum just to keep him on his toes.

All of this combined had the effect of keeping him perpetually horny and extremely eager to please me, exactly as I had intended. He knew that particularly good behavior would be rewarded with me rigorously pounding his asshole, and since this was the only way I allowed him to cum he was incentivized to be the perfect sissy. However, while I am not a cruel Mistress, I am a demanding one and if he did not sufficiently please me on any particular day, I would simply drop my load down his throat instead, leaving him wanting.

I can fondly remember one day when I came home to find him not in his usual kneeling position by the door, but instead on his hands and knees presenting his pink, well lubed asshole to me. I had been a bit mean with the vibrating plug that day and it had been a few since I had allowed him an orgasm. I think he hoped that his incredibly erotic display would turn me on to the point where I would just have my way with him right there on the floor. I was extremely tempted to do so of course, but knew that I had to keep absolute control at all times.

So instead I punished him for his audacity by locking him spread eagle onto his bed, gagging him, inserting a large vibrator and fixing his VR headset in place. I programmed it to only show the most depraved, explicit, goddess worshiping futa porn I could find and left him there overnight.

I did relent the next morning and fucked him to a sensational mutual orgasm though. Like I said I'm not cruel.

This went on for around a month and I couldn't have been happier.

Jamie was excelling, I had a live in fucktoy who couldn't get enough of my cock and my flat was always clean. Life was good.

There was just one more step to take.

DAY 91

It was another Saturday and I had the day off. What I was about to propose to Jamie had taken serious planning and would need my undivided attention. It had the potential to change both of our lives forever.

I called Jamie into the kitchen and told him to sit down. The stack of papers on the table and the look on my face told him how serious I was.

"What's going on?"

"Don't worry baby, everything is fine. I have something I want to discuss with you."

"Of course Mistress."

"I'm going to ask you some questions, and I want you to be completely honest, even if you think I won't like the answer, alright?"

He nodded.

"Are you happy like this, with what you've become, truly?"

He paused for only a moment before answering.

"Yes, absolutely."

"Why? In your own words."

He paused for longer this time, deep in thought.

"I feel like...like this is who I really am. Like I'm not pretending anymore."

"When I look at myself in the mirror, I like what I see. I like what you do to me, I like following your orders, I like pleasing you."

I smiled warmly. "Keep going."

"My life was so difficult for so long, I had no idea what I was doing. With you I feel safe, I feel cared for and that I don't have to worry about anything anymore."

"Does that make sense?"

"Of course it does. That's such a good answer baby."

"So submitting to me, not just sexually, but in all the other ways you have, that's what you enjoy?"

"Yes. The sex is incredible obviously but it's more than that. Being with you like this has only made my life better."

"So would you say that giving up control of your life to me has improved it?"

"Without a doubt. It's honestly been freeing, liberating even."

Yes! Yes fucking YES! I thought to myself, trying to keep a straight face and hide my excitement.

"In that case, read this."

I slid the top sheet of paper over to him.

It gave an overview of the contents of the contract, which was outlined in great detail in the rest of the document.

To put it briefly, the contract stated that Jamie would give up all his rights, privileges and possessions and would belong to me, as a pet.

Understandably, he looked a bit blank.

"Is this real?" he asked finally.

"Oh yes, a friend of mine is a very successful lawyer, and she helped me draft the document. It's been notarized, so if you sign, it's legal and binding."

"I know you're worried, but there are conditions. I can't permanently harm you, must provide shelter and provisions, must feed and clothe you appropriately, things like that."

"There's even a section specifically for appeal and annulment. If you truly believe that I am mistreating you then you can request counsel, and if they find me in breach, the contract is null and void and I have to compensate you a considerable amount."

"This is...I don't know what to say."

"What does your gut tell you?"

"It's telling me that this has been the absolute best experience of my life so far. But this..."

"I'm scared and excited beyond words."

"I understand how big this is. I'm not going to push you, or try and seduce you, or whisper honeyed words into your ear to make you sign."

"I want you to think clearly and openly and make your own choice."

"Here." I slid the entire contract over to him.

"Read it, take your time. I'll be in my room if you want to talk."

Reluctantly, I left him there, but I knew it was the right way to handle this. I couldn't force him to do this, and I didn't want to anyway. I wanted him to make this decision of his own free will. To realize how much better his life was with me and make the permanent choice to submit to me.

I sat nervously on my bed for an hour, trying in vain to concentrate on anything else. I went back to check on him and found him staring at the final page that needed his signature, pen in hand.

Oh my god, Oh my god, Oh my god. He's really going to do it!

He looked up as I approached and smiled.

"Promise me you'll take good care of me."

"I promise."

He signed the paper.

I looked down over his shoulder at our signatures.

Samantha Stevens -- Mistress/Owner

- - - - - - - - - - - - - - - - - - - - - - - - - - - - -

Jamie Wilson -- Sissy Slave

- - - - - - - - - - - - - - - - - - - - -

Holy shit! I fucking owned him!

"I'm so proud of you...my slave."

He was visibly shaking in his seat.

"On your bed now, naked, move!"

He ran off. I went into my room, stripped naked myself and picked up something I had been saving for this occasion. I hid it behind my back and went to find him.

He was sitting expectantly on his bed, completely naked as well, save of course for his cage.

"This is for you Slave."

I showed him what I had hidden.

It was a collar. Pink leather with a soft padded interior. A bone shaped golden metal tag hung from the front like a dogs and a lockable clasp closed round the back.

I held it up for him to read the tag.

'Sissy Cumdumpster'

He blushed and smiled, then held his hair up and out of the way.

I slipped the collar on, and locked it shut, sliding the key onto the chain round my neck next to the one for his cage.

"You look perfect Slave, now everyone will know what you are."

Looking at him like this, collared, caged, my slave...I could barely control myself. My cock was as hard as steel, pulsing and angry, pre-cum dribbling liberally from the head. This wouldn't be a long fuck, but it would be amazing.

"And now..." I pushed him onto his back.

"I need to bust a fat nut, and you deserve a reward."

I grabbed the bottle of lube that was always on his bedside table, squirted a thick stream of it onto my cock and climbed on top of him.

I lift his hips up a little and he wrapped his legs around my back, I lined up my cock and pushed inside him. Thanks to the massive coating of lube and his well trained asshole I was able to slowly but surely hilt myself in one long thrust.

Jamie let out a silent scream of unbridled pleasure. I shifted my weight forward, smothering his face in my tits whilst wrapping my arms down and around his back, pulling him tight into me. Since I'm quite a bit bigger than him all a casual observer would have been able to see of him were his ankles locked around my back and his arms wrapped around my neck. I wanted to completely crush him into the mattress.

With practiced ease, I drew back and pounded my cock deep into him. His ass was so accommodating, so receptive, so eager that I was able to slam my bitchbreaker down in long, powerful thrusts without any fear of harming him.

"That's right. Take it you fucking Slave."

Slam.

"Take my fat futa cock."

Slam.

"Who owns this ass? Tell me."

Slam.

"You do Mistress! You own meeeeee..."

Slam. Slam. Slam.

"You're nothing now, nothing but my sissy pet."

Slam. Slam.

"Nothing but a hole!"

Slam. Slam.

"My personal cock warmer!"

Slam.

"My!"

Slam.

"Sissy!"

Slam.

"CUMDUMP!"

Slam. Slam. Slam. Slam. Slam. Slam. Slam. Slam. Slam. Slam. Slam. Slam.

We came together, my thick sticky futa jizz blasting into the depths of his ass while his weak little load splattered out onto his belly. My orgasm just went on and on and on. I had him completely smothered by my body and could practically feel my load splashing into his belly.

At that moment, I felt completely unstoppable, like I could take on the world.

Eventually, I had packed his guts with so much cum that it started pouring out around my cock, even though his elastic asshole created the tightest possible seal.

I pulled out, watching a river of thick cum flow out of his abused hole. I left him, wallowing in a pool of jizz. I needed to make a phone call.

She picked up after a couple of rings.

"He signed it!"

"I know, I know."

"Yes I'm sure."

"Doesn't matter, I own his whole body now."

"It's amazing."

"Can you do tonight?"

"Perfect, see you then."

I hung up.

Later that night when the doorbell rang, I sent Jamie to answer it. He was only wearing his collar and panties but I didn't care. It seemed like he didn't either.

A tall punk woman with neon green hair and almost every inch of her skin covered in tattoos stood outside.

"Hey V! Come on in."

"Slave, this is Veronica, a friend of mine from uni."

By friend I of course also meant 'one of the many sweet pussies I tapped at uni', but in this case we did actually stay friends.

"Hi Jamie, everyone calls me V."

"Hello Miss V, how may I serve you?"

"Told you he was well trained" I smirked.

"V is here to complete your transformation sweetie. You're getting inked."

There was a flicker of fear across his features, but it quickly passed.

"Of course Mistress, whatever you desire."

"Still happy with the design we discussed Sam?"

"Absolutely."

"Great, no time to waste then."

Over the next couple of hours I happily watched Veronica work. She was a very talented artist, and the needle moved gracefully in her skilled hands. Jamie winced and occasionally moaned in pain, but I stroked his cheek to calm him. Soon enough, she was done.

I gazed upon Jamie's lower back. It now bore a stylized pink love heart surrounded by thorned red roses. It bore a message in the centre of the heart for all to see.

'Futa Cock Only'.

I smiled. It was perfect.