There's A First Time For Everything

by alectashadow

Tags: #cw:noncon #D/s #dom:female #dom:male #f/m #humiliation #pov:bottom #cocksucking #femboy #feminization #hypnosis #m/m #maid #maidification #microfiction #oral_sex #sissification #sissy #sub:male

Brian’s two roommates are very particular about his role in the household.

Life is a constellation of first times.

First  step, first word, first kiss, sure. But I have different kinds of first  on my mind at the moment, as I make sure my feminine wig is on  correctly, descending over my shoulders in a lustful, inviting mane.

Like the first time Susan smelled my weakness.

Even  then, I was a skinny boy, weak and short, with little facial hair. I  still see traces of that boy in the mirror, as I apply the blush – the  way Susan taught me to. The way most pleasing to Luke.

Luke  intimidated me the most at the time, of course. He embodied the  masculine ideal I could never match. But Susan was the one who first  realized I was such a pushover.

And… something a little more than that.

I  remember the first time she perentorily told me to do the dishes, even  though it was her turn. She just assumed I would comply, and she was  right.

Girls like her never had time for little wimps like me, so  by that time I had an ingrained Pavlovian reflex about doing what they  wanted, without expecting anything in return. Small-dicked mentality,  she called it once, laughing at my subservience.

Luke followed suit. Soon, I was doing his dishes, too. And the cleaning, and the ironing…

As  I trace slutty lines around my eyes, with my stripper nails glittering  pink and bright in the mirror, my mind wanders to the first time Susan  asked me to tie her shoes.

The first time Luke told me to cook dinner for him and the girl he was bringing home, so he could concentrate on fucking her.

The  lipstick feels good against my lips, pointy and hard. Luke once joked  that it was about the size of my little cockette, and that memory in  turn reminds me of the first time I heard the lock of my cage closing  around my emasculated manhood.

It jingles, even now, trapping my clit, binding it to the will of my two masters.

“That’s  the most precious possession of a man,” Susan once told me with an evil  smirk. “And you just gave it up. What does that make you?”

I  knew what that made me, and I know now. A small, increasingly distant  part of my brain tries to resist the concept, but satin and silk have  bound it entirely by now.

The skirt I was instructed to wear is a  fantastic fit for my wimpy figure, and is so frilly and short it barely  covers my cage. Luke’s rule – always be open and accessible. I have no  right to modesty.

This is the sort of stuff I fantasised about when I was still free – when I could touch myself whenever I wanted.

I  never shared it with anyone, of course, much less with my new  roommates. And yet, here I am, marvelling at the softness of pantyhose  as I roll them up my legs.

I know Luke likes the way I look in  them. I know Susan thinks it makes it clear that she’s the woman of the  house, and I’m the maid.

They clearly saw something in me from  the start. Soon after that initial exchange about the dishes, every  chore in the house had been delegated to me.

And that’s the first time I saw the pocket watch.

I  didn’t even have the time to question why anyone would own a pocket  watch these days. It was already swinging, as Susan whispered soft words  into my ears – words about femininity and softness and the best use for  small-dicked beta males.

I swirl before the mirror, pouting at  my imperfect display. I still have a while to go before I achieve the  lithe grace my masters demand of me. I think these thoughts without the  slightest hesitation now, but I was so scared then.

I remember  the first time I went to Luke for help and comfort, trying to flee  Susan. He effortlessly lifted me in the air with one arm – is that what  it feels like to be a girl, I thought back then, and now I know – and  said he had just the thing to help me.

That was the first time he showed me his pocket watch.

This  was a war on two fronts, one I couldn’t win. I buckled under the  assault, besieged on all sides. I offered my unconditional surrender as  Susan milked my masculinity out of me, stroke after stroke, while Luke’s  strong, wiry fingers explored every corner of my mouth.

Now, I am ready.

I stand on wobbly heels – I need to do better – and exit the bathroom, heading towards the living room, and the rest of my life.

I find my masters waiting for me.

Susan sits in the armchair like a queen, one leg draped over the other, fingers drumming expectantly on the armrest. And Luke…

He’s  claimed the sofa for himself, his hard cock already out, stiff and  glistening with precum. This is what a real cock should look like. Even  when it’s soft, it’s bigger than that pathetic clit they’ve locked away.

He deserves to win. To get the girls. To make me into his girl. To emasculate me.

I  curtsy, the way a slutty stripper maid is supposed to, and then sink to  my knees, the light reflected against my pantyhose as I present my cage  to my two conquerors.

Luke stands, copping a feel of my hosed  thighs, his dick wobbling left and right before my face. I hear the  click of Susan’s boots, as she comes to stand behind me.

She traces her fingers across my wig, delicately, almost in wonder. Then, they curl into a fist, taking a firm hold of my head.

“Ready, Peaches?” She asks, laughing at my whore name. Then, she pushes me forward.

Luke’s  cock enters my mouth the way a battering ram breaks open a gate, the  gate to my mind. I seal my lips around it, sliding back and forth. The  more of him enters me, the more my thoughts leak out of my brain, like  girlish precum.

“It’s your first time,” Susan says, her hand  regulating my pace, and of course, she’s right. It’s my first time  sucking cock, but I know for sure it won’t be the last.

As Luke’s  cock breaches the entrance to my throat, my eyes roll back into my  skull in pleasure, and I give out a slutty moan – the girly, submissive  moan only a true serving girl could give.

And in that moment, truly for the first time…

I surrender.

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