Worlds First Futa - Sissy Maid

After a minute, a new message arrived.

'Is it true?'

Bingo! She was mine now.

'Is what true hun?'

I was smirking as I wrote that.

'That you're an actual futa?'

'It's true'

'and you're packing a huge dick?'

'very true'

'no way, this is a prank right?'

I was prepared for this. Whilst we were texting, I had gone over to my desk and pulled out a 30cm ruler. I then dragged out my cock, pumped it a few times whilst thinking of Jamie to get it hard and then placed the ruler on top. It fit easily. Some of cock was showing on both sides of the ruler, and my head stuck out a good couple of inches past the end. I took a picture.

'does this look like a prank to you?'

I sent her the picture.

'holy shit!'

'think you could handle all that'

'I could more than handle it ;)'

She sent me a picture. She was stood with her back to a mirror, the phone pointed back over her shoulder. She had arched her back severely, pushing her ass up and out. It was one of the biggest asses I had ever seen. Round and jiggly and so very thick. It stood out even more so compared to her thin waist. Her booty shorts had been pulled up, showcasing a good portion of her smooth, caramel cheeks.

'not good enough'

That should keep her on her toes.

'What?!!!'

'My ass is amazing and you know it :('

'Yeah it's not bad, but you can show me more'

'All the simps following you online see pictures like that every day'

'Take it again, and do it naked'

There was a few moments delay then another photo arrived. She was in the exact same pose only now she was completely nude. Her sopping wet pussy was pointing right at the camera and it was drooling down her thighs. I could tell that sheathing my cock inside her was going to be biblical.

I sent her my address.

'Be here tonight, 8 pm, dress slutty'

'OK xxx'

Jamie arrived home a little while later. As we unloaded the groceries I told him the plan for tonight. I was going to be entertaining a female guest and he was going to serve us, in his maid outfit.

"Of course Mistress."

"Oh and Jamie, the guest is Maria."

He froze in shock.

"My ex Maria?"

"Is there a problem?"

"Well...I...I mean..."

I stalked closer to him, pinning him with my body against the counter. I gripped him very lightly by the throat.

"Is there...a problem?"

"Look at me!"

"No Mistress. No problem."

"Good girl. It's about time you truly learnt your place."

-

Come 8pm, everything was ready. The table was set and the food cooked. Jamie was wearing the full french maid outfit and I had upgraded it with new 4 inch heels. He would be tottering around a bit as he wasn't used to the size, but that only made his humiliation all the sweeter.

I had made an effort too. I had teased my hair into soft waves and put on enough make-up to be noticeable, but not whorish. I was wearing a tight fitting, dark blue sleeveless turtleneck without a bra over a pair of faded jeans that did absolutely nothing to hide my bulge. I also wore knee high, leather heeled boots. I looked damn good.

At 8:03, the door bell rang. I opted to answer it myself and give her a good long look at me. She also didn't know about Jamie, and I wanted her to be inside for that particular reveal.

I opened it and was treated to a real feast for the eyes. Maria was wearing a white dress with a plunging neckline that barely contained her prodigious tits and stopped a few inches above mid thigh. I think it was supposed to be longer, but her giant ass took up so much room in the back. There were slits down each side connected with thin that went all the way from under her arms to the hem of the dress which meant I could easily see almost all of hers legs and all the way up her sides. It also made it very obvious that she wasn't wearing any underwear. She was also wearing heels, with straps that twisted round her lower legs up to her knees

Overall, I would say she was an absolute, 10 out of 10 club slut.

I grabbed her by the waist and pulled her in to a fierce kiss.

"Maria, baby, you look hot as fuck."

She seemed a little taken aback by my boldness but smiled at the compliment. Besides, we both knew what she was here for.

I showed her inside and shut the door.

We sat down and Jamie came through carrying our meals.

"Let me introduce you to my housemaid, Jamie."

"Hi Jamie, thanky- wait, no way, the Jamie?"

"The one and same. Though she has changed a bit over the last month."

"Oh my god, he...she looks so pretty. I knew you weren't manly before but this...wow."

At this point I think Jamie wanted to melt into the floor from embarrassment.

"That's because he was never truly a man. He's a sissy girl. My sissy."

"Isn't that right sweetie?" I asked him.

"Yes Mistress." Maria laughed gleefully when he called me this.

"And who do you belong to?"

"You Mistress, I'm yours."

"Good girl, now show Maria your cage."

I almost thought he wouldn't do it, but slowly, with trembling hands, he lifted up the front of his skirt and revealed his tiny chastity cage.

He needed this, needed to understand his place at the bottom of the proverbial food chain. I was at the top, always. Followed by my friends and partners. At the bottom was him, barely more status than a fleshlight. He had to understand that he was lucky to get my attention, and even luckier to get my cock.

Maria was biting her lip as she fondled his caged cock.

"This is so hot. He really is a total sissy."

"That's right. It's actually the reason I invited you here specifically. Well, one of two reasons."

"Oh?"

"Yeah. He needs to understand his place in my world."

I grabbed his cock and balls and twisted just enough to hurt.

"He is my sissy, he belongs to me."

I looked him meaningfully in the eye.

"That includes his tight little asshole."

Realization dawned across his face, followed quickly by acceptance. My work here was done. I released his cock.

"And the second reason?" Maria asked. I could see she was already fidgeting and I could smell her arousal. No doubt she was leaking all over her seat. I would have to get Jamie to lick it clean later.

"I want to ruin your pussy with my huge futa cock, obviously!"

Maria visibly shivered at my words and gripped the table. I think she may have had a tiny orgasm.

Fuck it, I thought. I'll eat later.

"You know what, we're skipping dinner."

I stood up and pointed at Jamie.

"You, go your room and listen well. You're going to hear your ex get properly fucked for the first time."

I pointed at Maria.

"And you, come with me."

Once we got to the bedroom, I pulled Maria into my arms and kissed her again. It was rough and ferocious. She could barely keep up.

I spun her around and pushed her forward so that she was bent over the side of the bed. I peeled her dress up and revealed her ass. God damn it was glorious, huge, fat and jiggling. This was the definition of booty.

I spanked it with all my might just to watch it wobble.

I undid my jeans and pulled out my cock. It rapidly hardened at the prospect of plunging inside the dripping pussy in front of me.

Maria looked back at it in absolute awe.

"I NEED that inside me. Don't hold back."

She lowered her head and raised her ass even higher. I needed no further invitation. I grabbed her hips and thrust into her. She screamed.

After that I fucked her like I was possessed. I used every last ounce of my strength to slam my entire cock into her over and over and over again. I wanted to teach Jamie a lesson and needed him to hear her, to understand that I could give her much more than he ever could. I needed him to understand what a sissy he was.

Her pussy was eager for my cock, sucking me in and clamping down whenever she came, which seemed to be practically non-stop. My cock was in pussy heaven, rampaging into an eager womb that was wide open and begging for my cum, but I held back.

I wanted to display my prowess, my self control and my stamina. I wanted to completely wreck this cunt and further drive home my point to Jamie, humiliating him even more.

By this point, Maria's arms had given out and she was flat on her front, only her ass pointed upwards. I began spanking her in time with my thrusts, calling her a filthy whore, a slut, cumdumpster, a useless bitch only good for taking the biggest cocks. Her only response was to moan even louder and keep pumping her ass back onto me.

Eventually I found the perfect rhythm, each mighty thrust of my hips causing her ass cheeks to clap into each other loud and hard. At the same time, my hefty balls would swing forward causing a wet slap as they smacked into her clit. Maria seemed almost comatose from the sheer pleasure.

I decided that I had showed them both how serious I was, and let down my mental barriers. After a few more pumps, I pulled her hips all the way back until her ass was squashed right up against me and my cock was pressed up to her cervix. I came and came, rivers of thick white cum unloading into the absolute deepest parts of her. I screamed out my pleasure, wanting Jamie to know I was seeding his ex. I kept her held there, completely impaled, until I stopped shaking and my balls stopped pumping.

I pulled out, my cock sliding free with a disgusting schlorp. Once she was uncorked, the full extent of the carnage I had caused was revealed. Her pussy was splayed wide open, ragged and red. Thick globs of my cum ran freely from her ruined hole. She was gurgling incoherently.

"JAMIE!" I called. "Get your ass in here and clean up this mess."

He came running in, stopping dead when he saw what was left of his ex-girlfriend. I think he wanted to run right back out, but the sight and smell of all that delicious futa cum got to him. Instead, he dove right in, sucking and slurping obscenely at the mess between her legs.

I sauntered back into the kitchen and left the happy couple to it. I chugged a glass of water and ate my fill. I went back to check on them and found Maria still zoned out in the same position as Jamie continued to happily lick away. He had done an admirable job of cleaning her up, the only cum I could see now was slathered all over his face.

I pulled Maria to her feet and started frog marching her towards the door.

"Come on slut, you served your purpose, time to leave."

She staggered along on very shaky legs. I got her to the door and pushed her out into the hallway.

"Wait, please, can I see you again?"

She looked a lot less sure of yourself now than when she arrived. Her hair was a mess, her skirt had ridden up practically exposing her pussy and one of her tits was hanging out.

"Why should I? I got everything I needed."

"But, but, your cock...it was so...nothing else compares."

"Tell you what, you're a fine piece of ass and I'm going to bet you know a whole bunch of other sluts from the club and that gym you work at. You tell them all about me and I might consider blowing out your hot pussy again."

"Of course. I'll tell them all. I'll-"

"We're done." I slammed the door in her face.

I found Jamie in the bathroom, washing his face.

"Do you understand now? Do you know what I was trying to teach you?"

"Yes. That I really am a sissy. That I could never fuck a girl like that."

"And...If you can't fuck, what should you be doing?"

"Getting fucked by my Mistress."

I chuckled and smiled warmly. He smiled timidly back, I think I had finally gotten through to him.

"That's right my precious girl. Don't worry, I'll be much more gentle with your ass the first time than I was with Maria. I was just making a point."

"Thank you Mistress."

"That's settled then. I'm going to go online and order lots of toys and lube for you to practice with. Then when you're ready, you know what to do."

-

I spent some time the next day going an anal toy shopping spree. I purchased a gallon of lube, a buttplug training kit, 2 set of anal beads, a prostate massager and a smaller 6 inch dildo.

Once they arrived, I set about adding them to his existing daily routine. I wanted him good and prepared for his first time and I was still serious about not fucking him until he begged me to do it. My cock was angry with me, and wanted nothing more than to bend him over and fuck his ass into oblivion but I sated it with regular blowjobs, of which Jamie was becoming quite the expert.

Jamie was required now to wear a buttplug at all times. I started him small, but every couple of days would increase the size until he was comfortably wearing the largest plug. At it's widest, it was just a little thinner than my cock. I couldn't wait for that exquisite stretching feeling when I entered him.

I also started teaching him about his prostate and how to have a sissygasm. He seemed very pleased when I explained that it was still possible for him to cum whilst in chastity. When I first used the prostate massager on him, he literally squealed in pleasure. I thought he might cum on the spot! His p-spot was clearly very, very sensitive. I told him that when I crushed it with my cock, he would squirt like a real girl.

Training and playing with his ass became my new favorite pastime. I would often spend a few hours each evening teasing him, stretching him and making him moan. It was during one of these sessions that he finally gave in, sealing his submission to me forever.

DAY 58

I had just finished my dinner and was relaxing on the sofa whilst Jamie cleaned the dishes. I turned and looked back towards the kitchen as it was always enjoyable to watch him work. I had opted to have him be completely naked today, and all he wore at the moment was a short apron to protect him from splashes of hot water. His luscious ass was on display, the metal tip of his plug peeking out from between his cheeks and his little cage dangled down.

I wanted him badly.

As if sensing my gaze, he turned and looked back over his shoulder. Confirming I was watching him, he winked at me and bent forward more, slowly waving his ass back and forth. This sort of behavior had been happening more and more lately. I think that as he got comfortable with becoming a sissy, his confidence in his womanly body grew.

I also think that since he knew how badly I wanted to fuck him, he took no small pleasure in teasing me like this. In fact, it had almost become a battle of wills to see who would break first. Would he give in and beg to be fucked, or would I lose my self-control and roughly take him. We both desperately wanted the end result, my cock utterly filling his ass, but this twisted game of cat and mouse was very entertaining for both of us.

I was going to win, because I had an advantage and knew his weakness.

My advantage was that I was able to cum, if I got too horny and thought about bending him over and ravaging him, I would just blow a load down his throat instead. He on the other hand had not cum in weeks. I knew that every time I played with his ass, teased his prostate, slid my fingers in and out of him, he was getting ever more desperate for that sweet release.

Last night I was sure he was going to give up, but he just barely kept his composure.

Tonight. Tonight I would make him mine.

"I'm finished Mistress. May I go to my room?"

"Not just yet sissy. Come here."

Ever the well behaved girl, Jamie came over and stood beside me awaiting his next order.

"I'm very much in the mood tonight, so we're going to have a serious session."

"Go and fetch all your toys and lay them out by the bed."

"I'm going to go get changed into something a bit more...suitable."

He knew that my dressing up meant I was very serious.

"Oh, and put on those socks I love, you know the ones."

"Yes Mistress."

He kept his composure as I explained this, but I caught a glimpse of a huge grin on his face as he ran off.

I went into my room and stripped naked. Thinking about what I wanted to happen really had my blood pumping, so I decided to go for full Dominatrix mode.

I dressed myself in a black leather half bust corset that pushed my tits up and together into a valley of cleavage, black silk arm gloves that went all the way up to my bicep and thigh high black leather stiletto boots that laced all the way up the back of each leg. I also added some dark eyeliner and cherry red lipstick. I looked hot and dangerous.

When I walked into his room, I was very pleased to find Jamie face down ass up on the bed. All of his various toys were ready alongside him. He had put on my favorite socks too, knee high white cotton socks that were dotted with pale pink love hearts. They made him look incredibly girly.

Tall, dark, sexy, dominant.

Small, pale, weak, submissive.

We were the picture of opposites.

I strode over to him and spanked his ass hard. He squeaked in pleasure and pain but held his position.

"You look so good like this pet. What a sexy sissy girl you've become."

"Thank you Mistress. Thank you for showing me who I was meant to be."

I reached down and gripped the tail of the plug, and very slowly pulled it free, pausing to let his ass stretch wide around the thickest part. I could hear his breathing get faster and saw his hands tense and grip the sheets. He groaned as it popped free.

I slapped my cock down between his cheeks and sawed it back and forth. His ass was so fat and bubbly that I could easily hot dog my shaft in between them. He rocked his hips in time with me, creating a delicious friction.

"Ready to beg yet sissy? Just imagine all of this inside you?"

He opened his mouth to answer, but caught himself at the last moment. Instead he blushed and shook his head, but he was grinning at me. The game was well and truly on now.

"You little minx!"

"I'll have you begging before the night is over."

I slipped a finger inside him and pressed down lightly on his prostate. He squirmed and moaned.

"I know how much you need to cum."

I pulled back and picked up a long set of beads, each bigger than the last.

"Lets start with these."

Over the next hour, I mercilessly teased and tormented his asshole with every manner of toy.

I crammed his ass with the beads, pulling them out in a staccato rhythm to keep him guessing. I fucked him with a dildo, using the attached tube to pump him full of lube as if someone were cumming inside him. I filled him with a large vibrating plug, set it to maximum and paddled his cheeks raw until he cried out from the sweet agony.

I knew he must be close because when I inserted my fingers and probed him, I could physically feel the walnut sized lump of his prostate, swollen with backed up cum. His little balls were twitching and his whole lower body occasionally spasmed. If he hadn't been caged, I think one touch of his cock would have set him off instantly.

I cupped his balls in one hand and rolled them around whilst with the other, I rubbed two fingers strongly back and forth across his p-spot. He had his eyes shut tight and was moaning and squealing in sheer bliss.

So I stopped.

I can't imagine the torment this must have caused him.

"Please..." I heard him whisper.

"I need to cum Mistress. It hurts."

"You know I won't let you cum until I fuck you."

I placed the tip of my cock at his entrance and applied the tiniest amount of pressure for emphasis.

"Please..."

He was nearly there.

"You know how good my fingers and the dildo felt, just imagine what will happen when I bury my fat futa cock inside you."

"I need to cum so baaad."

"You know what you have to say to make that happen sissy."

There was a very pregnant pause, and then...

"Please fuck me Mistress. Please!"

There it was. I had won. It was moments like this that gave me the most incredible feeling of power and potency. I had taken this boy, humiliated him, degraded him, feminized him and now he was literally begging me to plunder his asshole.