Worlds First Futa - Sissy Maid

Jamie was dumbstruck, I had essentially just offered him sexual servitude. I was counting on the fact that he had no other options.

"Well, what's it gonna be Sissy?"

I drew out the last word for emphasis, I wanted to really highlight exactly what his new role was going to be.

"Will you...will you want to fuck my ass?"

Holy shit! I thought. Is that really where his train of thought went? Not concern over where he was going to stay, or my telling him I was going to turn him into a girl, but whether or not I was going to fuck his ass? Incredible.

"Oh my sweet sissy, I already want to."

There was fear in his eyes, but deeper I could sense the first burgeoning embers of desire as well.

"But I am not a cruel Mistress, and I know this whole situation must be pretty intense. So I'll make you a deal."

I stepped over to him and leaned against the table next to him. I angled myself so that the thick bulge of my semi hard cock was clearly visible to him through my tights.

"If you follow all my other rules, I won't fuck your ass...until you beg for it."

I chuckled softly at his discomfort at the thought, and yet he couldn't tear his eyes away from my cock.

"I need to go to work soon, so I'll give you time to decide. Once I go, you may leave if you wish and go wherever else you want. If when I return this evening, you are still here and the flat is spotless, then I will take that as agreement to all my conditions."

I took his hand and placed it on my bulge.

"I know you want this Sissy, don't disappoint me."

I quickly stood up, grabbed my coat and bag and left him sat there, deep in thought.

-

When I opened the door later that evening, I found Jamie waiting for me, wearing his pinny and brewing a fresh pot of coffee. Such a good boy.

-

Over the next few weeks I slowly eased him into his new lifestyle. I started by giving him the full french maid outfit, I figured that if he could handle that and didn't run he could handle anything in the end. I did let him wear flat black pumps for now though, his heels training would come later.

To my surprise and joy he took it without complaint, got changed into it and got to work. He couldn't look me in the eye the rest of the day for embarrassment though. It really was very cute.

I ordered him to wax himself and let his hair grow out. The waxing was pretty painless, he barely had any body hair to begin with. I was overjoyed when I asked him how it felt later and he said that his maid stockings felt really nice on his newly smooth legs.

I started him on a new fitness regime that featured heavily on his ass and legs, no upper body exercises allowed. It featured plenty of lunges, hip thrusts and squats. Of course I made sure he exercised while wearing some of Em's old workout gear. After only a week his ass was really starting to pop out of the Lycra.

Finally, I had him start learning how to properly apply make-up. I allowed him to keep it clean and simple around the flat, but had him practice more advanced techniques like smoky eyes as well.

Of course on top of all this he practiced his most important duty, satisfying my huge cock and draining my heavy balls whenever I needed it, which was often.

I didn't push him in this regard either, and was content for him to use only his hands for now. He quickly gained in skill and experience. To keep up the power dynamic, I would always have him strip down to just his panties and liberally cover him with cum each time. I even took to keeping an XL bottle of lube prominently displayed on the coffee table that he would use each time I needed release. After the first week, he seemed to learn from my body language and demeanor when I was getting pent up, and would willingly offer his services.

Overall, I was very pleased with his progress and he was taking it to it very well, dare I say even enjoying it. I would often find him browsing for make-up tips or looking at women's hairstyles online in an evening. I didn't even have to tell him to do so!

He was becoming more and more of a Sissy every day, so I decided it was time to go further.

DAY 35

When I got home that evening Jamie was preparing dinner in the kitchen. He looked wonderful in his maid outfit, the picture of domestic bliss. I called him through into the hallway.

"Hi Mistress" he chirped happily, long ago having learned that's what he should call me.

"Come over here Jamie, there's something new I want you to learn."

Once he was stood in front of me I ordered him to kneel. Once he was down I re-positioned him so that his lower legs were flat along the floor, his butt resting on his heels with his head up and back slightly arched. I then placed his hands on his inner thighs. This is a classic submissive 'presenting' position, that shows the sub is ready for their next order.

"Good boy" I said. "You look lovely like this. From today on, I want you to present yourself like this to me every time I come home each night."

"Of course Mistress."

"You know, I really am pleased with your progress. Why don't you go get us some wine while I get undressed then come and join me on the sofa."

I stroked his cheek affectionately then walked off.

I hung up my coat then stripped out of my shirt and skirt leaving myself wearing only my underwear and stockings. I stretched and sat down, happy to be home after a long day at work. Jamie came through carrying a bottle of wine and two glasses. He looked so cute in his uniform, the little white bonnet on his head, the sheer white stockings that gave him a virginal look, the short silk skirt that only just barely covered the swell of his ass, I could watch him work like that for hours.

He poured me a glass and then stood to one side, waiting. His training was really paying off.

"It's ok, relax, sit down and pour yourself a glass."

"Thank you Mistress."

He poured his wine then sat down gingerly next to me. It was rare I allowed him these comforts around me so I knew he would be nervous. He had been very well behaved recently though, so I wanted to reward him for that and simultaneously push his boundaries further.

"Come here baby" I said, wrapping my arm around his shoulders and pulling him into me so that his cheek was resting on the swell of my bosom. He snuggled into me and sighed happily. I let us sit like that for a little while, both of us enjoying a tender moment and the wine.

"You've been enjoying all of this, haven't you?"

He didn't answer at first, still too shy perhaps. I swatted him lightly on the backside.

"Haven't you Sissy?"

"Yes Mistress" he squeaked.

"You like being made into a girl?" I asked, a little bit of a mocking tone to my voice.

"Yes I do. I like feeling all soft and smooth. I like looking cute in my clothes. I like the way I look in make-up. It all feels good, feels right somehow."

"Oh I know you do. It's because you're a little sissy bitch."

He looked a little hurt at that last comment.

"It's alright pet, that's not a bad thing. Not all men can be big, strong alphas. Boys like you should understand their place and be happy for it."

"Besides, I like Sissy boys..."

This seemed to calm him and he snuggled even tighter into me. I noticed his breathing get shallower and his hand started to creep up my thigh towards my bulging thong.

"I see you like me too..."

His small, dainty hand cupped my cock and I groaned in pleasure.

"Tell me what you like about me baby" I said, grinding myself slightly against his hand.

"You're so beautiful Mistress, and your body is incredible. I like everything about you."

"Ooh, you're earning plenty of brownie points today."

"What do you like best? Is it my face? My soft, plump lips?"

He shook his head and blushed.

"Is it my tits then? I know how much you loved it when I let you suckle on my nipples."

He shook his head again, his blush becoming a deep crimson.

I lifted my hips then slipped my thong down and off my legs with practiced ease. My cock rose quickly, bobbing in the air. He gripped onto it by reflex.

"Is it my big, throbbing futa cock that you love?"

He was staring at it, mouth agape and practically watering, as it always was whenever I revealed myself.

He nodded slowly.

"Then don't you think it's time you learnt how to suck it?"

He nodded slowly again.

"Then get down on your knees like a good boy, it's time to properly worship your goddess."

He slid off the sofa and positioned himself between my spread legs. I shuffled forward slightly, letting my full cock and balls dangle over the edge. He would need to get very used to being in this position from now on.

The tip of my cock bobbed around an inch from his lips, just beneath his nose. I watched as he took a few deep breaths, this close my musk would be strong and he was already mildly addicted to it.

"Kiss it" I ordered.

He puckered his soft, fat lips and gently kissed my tip. My cock throbbed in response and dollop of pre leaked out. He kissed it again, tasting me for the first time. I saw his pupils dilate slightly at the sensation. There was no escape for him now.

He kissed the tip again and again, each time becoming sloppier and louder.

"That's it Sissy. I already knew you were a dirty panty sniffer, but the real thing is so much better isn't it?"

He nodded happily, too busy making out with my cock to respond with words.

"Don't forget my balls sweetie."

He ducked down, scooped up my dangling balls in his hands and ran his tongue all over them. Jamie was in sweaty ball heaven, licking, slurping and generally rubbing my swollen sack all over his face. He was humming in delight. The taste and smell must have been overwhelming for him.

"Urgh, yes. That's it you little cocksucker. Spit shine my balls. Work up a nice big load. If you think that tastes good just wait til you swallow my load."

His hands both came up and resumed swiftly jacking my cock above his head. He took an entire orb into his mouth with a wet pop and kept sucking. His hot mouth and practiced hands felt heavenly, and I soon realized I was closer to cumming than I thought.

"I'm getting close bitch, get back to sucking."

Jamie's head came up swiftly, already drooling he dove onto my cock, hoovering the head and a couple extra inches into his mouth. He technique was inexpert, but his enthusiasm and eagerness were unmatched. It was quickly turning into one of the sloppiest, messiest blowjobs I had experienced. Watching his plump, girly lips slobber and slide up and down my shaft was sublime.

I knew he wouldn't be able to take the whole thing, but his earlier efforts on my balls had them practically churning. Besides, I wanted him to taste every drop of this load.

"I'm gonna cum Sissy, get ready for your first taste of heaven. Hands on my balls, now!"

He did as he was told, rolling my heavy cum factories in his hands. I pulled back til just the head remained in his mouth and vigorously jerked the rest with both hands. He looked up at me with absolute adoration in his eyes.

"Don't you...dare...waste any." I grunted, right on the edge.

"Swallow...it...alllll!"

I came. Hard.

The attention he had given to my balls had them producing a gigantic load. It shot forth in streams from my cock, splashing thickly into his mouth and throat. I watched, impressed, as his lips clamped down around the head and his cheeks ballooned out from the sheer amount but he kept swallowing and swallowing as I kept feeding him. I could see his neck pulse and contract in time with every burst from my cock.

After a while, my orgasm began to ebb. Only a few straw strands had escaped his lips and were dribbling down his chin. I pulled back and watched him swallow the last considerable mouthful, breathing hard.

"You must have wanted that bad, you swallowed almost of it you greedy little cum whore."

"You taste so good Mistress, it was so thick and creamy."

"And what do you say when Mistress gives you what you want?"

"Thank you Mistress, thank you for feeding me your cum."

"What a good little Sissy you are!"

"In fact, you've been so good recently I think you deserve a reward."

"Lay on your back and take your panties off."

Jamie eagerly did as he was told. I stood over him and he seemed to be of the delusion that I was going to ride him.

I laughed in his face.

"Oh no sweetie, I only indulge my pussy on very special occasions, and certainly not with a little girl like you. But don't worry, your tiny clitty is still going to get some attention."

He winced at my words, but I could still see the hunger in his eyes. I had been instructing him that he was no longer to masturbate and I'd hadn't let him orgasm since he moved in with me. I could see that that his dick was raging hard, at his 'full' length of 3 inches.

I was going to let him cum, but not without some serious emasculation and humiliation at the same time. I was hoping he would come to associate those feelings with his orgasm.

"Look at this" I said, bending at the waist and flipping his short skirt out of the way.

"It's pathetic." I flicked the tip lightly for emphasis, he squealed and his hips bucked up off the ground.

"You were clearly born to be a sissy girl."

He looked to be on the verge of tears. I think some small shreds of masculinity still remained. I would have to work on that.

I lifted my foot, and slowly began to caress his shaft with my toes. The silk material of the stockings allowing my foot to glide ever so smoothly. I could already feel him twitching.

"Do you really think Maria would have been satisfied by this? That any woman would be?"

"No-ahhh...No Mistress."

"Do you think a real man would have a cock like this?"

"No Mistress. Oh my goooddd..."

I applied some more pressure, and started working the little head with my toes. His hips were jumping and he had a death grip on the rug.

"So if you're not a man, what does that make you?"

"I'm a...I'm a...a sissy." He was saying the right words, but I wasn't convinced he truly meant them yet.

"Say it again slut, loudly, and you can cum."

I put on even more pressure and stroked my foot quickly back and forth. I knew there was no way he would be able to hold back.

"I'm a Sissy!" he moaned loudly, cumming hard. His whole body tensed up and a few tiny spurts of runny cum dribbled out of his cock onto his belly and my toes. It was over in a matter of seconds.

"Clean up your mess Sissy" I ordered, proffering my soiled toes.

He subserviently stuck out his tongue and lapped up his own cum.

"There's a good girl. Now that's out of the way, there one other matter to take care for tonight. Stay here."

I left him panting on the floor and went to pick up a box from my wardrobe. It contained a custom ordered XS 'Sissy in Pink' chastity cage.

I took it back into the living room and handed it to him.

"Put it on."

He looked at me blankly. I don't think he quite believed what he was holding in his hands.

"I'll make this simple. You are a Sissy. Sissies get locked away. Put it on. Now!"

He whimpered, but didn't argue.

He opened the box and carefully followed the instructions. His limp little cock was so soft after his orgasm that the cage fit easily, even given its small size. All that remained was the lock. I picked that up from the box myself, slid it into place, then slowly and deliberately pushed it closed.

There was a very definite 'click'.

I knelt down and mockingly kissed his new cage. I then took the key, slipped it onto a slim silver chain and hung it round my neck. It rested enticingly between my tits.

Jamie looked defeated, yet resigned to his fate.

"Good girl, now clean yourself up and go make us dinner."

-

Another week or so later, Jamie was still progressing nicely. His daily routine now consisted of waking an hour before my alarm to prepare breakfast, before slipping into my room at the appointed time and crawling under the covers. I awoke each day to him nuzzling on my balls, before he proceeded with one of his fantastically sloppy blowjobs and the first load of the day down his throat.

He has admitted to me that this is the favorite part of his day. He told me that as my cock often leaks a little pre-cum during the night, the area under the sheets becomes hot, sticky and sweaty each morning. The little cum guzzler was rapidly becoming more and more addicted to me.

After the morning blowjob, he would don his uniform, which now included 2 inch heels and proceed to serve me breakfast before I showered and left for work. He spent most of the day cleaning and any free time was to be spent practicing his make-up, styling his hair and meticulously shaving and plucking every last hair from his eyebrows down. His hair had grown another inch or so over the last month and it was becoming nigh impossible to recognize him as a boy at all.

I had also installed a 12 inch 'Black Mamba' dildo to a full length mirror in the living room. It wasn't quite as big as me, but the practice wouldn't hurt. I found it very amusing to watch him repeatedly fuck his own throat while staring at himself dolled up in ultra feminine clothes. I often had to put a towel down to deal with all the excess drool. He could take all of me down to the balls, but I hadn't yet removed his gag reflex entirely so more practice was required.

He also never once complained about the chastity cage though I would see him eyeing the key around my neck occasionally. I had taken to telling him that I would only let him cum again when my cock was buried balls deep in his tight ass. I knew his resolve was faltering on the issue and with enough time he would come to me, pleading to be fucked.

As usual however, my cock had ideas of it's own. It was like a bull to a red flag every time I saw him bend over. It wanted in that ass, and it wanted it now!

One day, I had epiphany. I thought of a way to convince him what a sissy he truly was, get him desperate to have his sweet ass fucked and add another ruined pussy to my extensive list of conquests all in one fell swoop.

DAY 44

It was glorious Saturday in the middle of summer. I had just sent Jamie on an errand to go get some groceries. Since we were still building up his confidence in public, I sent him out in a knee length skirt, simple t-shirt and trainers, with his hair up in a ponytail and minimal make-up. He could have easily passed as someones little sister so I knew he would be fine.

While he was out, I stole into his room and took his phone. I had seem him use it enough in the past to know the pass code. Once logged in, I searched through his contacts until I found Maria, copied her number into my phone and then put his back where I found it.

I immediately set about seducing her. From what Jamie had told me of there last conversation, I didn't think it would be difficult.

I debated internally on how to approach things, but after a little research via her social media accounts, it became obvious how I should proceed. This girl was a total slut! Almost everything she posted included a picture of her in either tight gym wear, a very revealing dress in some club or a bikini. It seems her abstention from her whorish ways with Jamie was well and truly over.

This would be almost too easy. I set about texting her with gusto.

'Hey Maria x'

'Who is this?'

'It's Sam, Sam Stevens. I think Jamie may have mentioned me'

'Oh right, are you the Sam he worked for?'

'That's me'

Yeah I'm that Sam, I thought. I'm the Sam with the humongous cock that Jamie told you all about. There's no way a girl like her would forget that.

The three little dots signifying a message being typed appeared and disappeared a few times. Come on, ask about it, I know you want to, I thought to myself whilst staring intently at my phone screen.