Sissy Holidays

This happened one hot summer, when the exams were already over, and it was time to look for a side job for the remaining months. This time it wasn't so easy; I didn't want to hang around the job our Institute offered again, so I decided to scour the ads in newspapers and online. The first week of searching yielded nothing, and I was starting to despair, when suddenly, on one of the forums, I found a post: "Maid needed for a private house, high pay, live-in position."

Without thinking twice, I dialed the number. A pleasant, velvety female voice on the phone assured me I could come over today, and if everything suited them, I could start right away. Taking

this as a kind of gift from fate, I quickly got ready and went to the specified address. It turned out to be a cottage house in the center of a guarded settlement near our town, surrounded by a coniferous forest, quiet. The house was surrounded by a high fence with decorative iron spikes on top. I pressed the doorbell button and after a while heard approaching footsteps. The door opened.

A woman, about forty years old, stood before me. Her straight dark hair was tied in a ponytail, a thin dress elegantly hugged her body, very slim for her age. Glancing, I noticed she wasn't wearing a bra. Trying not to look at her chest anymore, I stared at the floor, at her feet with black nail polish in sandals, and blurted out:

— Hello, I'm the one who called about the ad.

The woman gave me an appraising look, lingered slightly on my bangs (I wore a choppy fringe over one eye like many from 2007 back then) and, gliding over my thin frame, said:

— Yes, we were expecting you. Come in, we'll talk inside.

The door closed behind me; I heard the lock click. We walked along a path paved with cobblestones to the house, whose massive stone porch was made in an ancient Greek style. Corinthian columns, I think, if I haven't forgotten my history yet. She pushed the heavy doors with her hand and they opened easily and silently. We found ourselves in a cool hallway; after the daytime heat, I felt a bit languid and was very glad for the offer to sit in an armchair.

— I'll explain the details of your work, young man, — she put a special emphasis on the word 'young man', — we need a maid in the house. Actually, we were looking for a girl; they are neater. But if you say you can handle it just as well, then we'll take you, but with a probationary period. You'll need to wear a uniform and keep the house clean, and, well, various small requests. You'll live here, in one of the rooms. Besides me, my two daughters live here. We are a female collective, so you understand, we will take some measures to prevent unforeseen situations. Are you okay with that?

— Yes, I agree. The pay will be as you said before, right?

— Yes, and much more if you manage to do everything on time. Small bonuses at the end of the month. Then come, I'll show you your room.

We went up the stairs to the second floor. The bare feet of the lady of the house softly stepped on the carpet; apparently no one wore shoes here, I looked a bit silly in socks, but what could I do. The room turned out to be small but bright, with a bed in the corner, a wardrobe, and a mirror. The wallpaper was a soft pink shade. Catching my glance, Damira—that was the lady of the house's name—answered:

— As you can see, the room is a bit feminine, but we weren't expecting a boy, so don't be shy, make yourself at home, and I'll bring your uniform.

She left and, judging by the footsteps, headed downstairs to the first floor. I quickly looked around the room; nothing interesting. Judging by the size of the house, there were at least a dozen such rooms here, and I'd have to clean them all. I could only hope not all of them were occupied.

— Here it is, — the woman placed a bundle of clothes on the bed, — put it on, let's see if the size fits.

— Y-you want me to change in front of you?

— Nothing to be shy about, what haven't I seen? Especially since your job involves close contact; we won't take a sick person. I need to examine you.

Blushing like a freshman, I started taking off my clothes. There wasn't much, until I was left in just my underwear. Of course, she demanded I take those off too, and my boxers flew into the general pile.

— Hmm, what luck. — I tried not to look down as she felt my cock, — wait a second.

She took a small box from the bundle of clothes and opened it. Inside were a plastic tube and rings of different sizes.

— You don't know what this is? — she nodded at the thing.

— N-no, sorry.

— It's a chastity belt. It's put on when they don't want a man to commit rash acts. As I said, I have two daughters in the house, your age. I don't know you, and I won't take the word of a boy in the prime of puberty. Put it on.

— B-but, this, this is, you can't do that.

— You can gather your things and leave right now. No one is holding you. But then you'll get nothing. Or you can put on this little thing and get everything I promised you. Choose. By the way, what bothers you so much? Or were you planning to jerk off in secret here?

— Blushing even more, I lowered my gaze and reached out my hand. Clumsily trying to pull the plastic onto my cock only aroused it, causing it to start getting hard.

— That won't do, let me. — She lubricated my cock with some gel; it immediately felt cold, but the erection subsided. She put the plastic on my cock, fastened the ring on my scrotum, and locked it. — The key will be kept by me. I will give it to you on a schedule. The anesthetic effect will wear off soon, don't worry. Now, let's proceed to the rest.

The lady critically looked over my body; she especially didn't like the hair on my legs.

— Those will have to be shaved. Though that's too long, so follow me.

I followed Damira out; we went down the corridor to the bathroom. How huge it was. Nothing like in my parents' apartment. The center of the bathroom was occupied by a huge jacuzzi, capable of holding five people. The ceiling and walls were covered with mirrors, so you could see yourself from anywhere. Damira brought a bottle with some gel and treated my legs, armpits, and... the bikini area. I decided not to be shy about anything; the salary was worth it, and I really needed it. After a few minutes, I was already rinsing the hair off myself in the shower.

— That's much better, let's go. — We returned to my room, where I started putting on the pieces of the uniform. A very strange uniform for a boy, let's say. — We thought we'd have a maid; the girls wanted a servant like the French have. I don't know where they got that from, but you'll be walking around in this.

I looked at myself in the mirror and, contrary to my promise not to be surprised, froze with my eyes wide open. I was looking at myself, but in a black and white lace dress, white knee-high socks, heeled shoes (how uncomfortable they were!), and a bow on the back.

— Today I helped you dress, but on regular days you'll have to do it yourself. She handed me a set of tools—brushes, rags, and other cleaning supplies. — The girls will be back soon, take care of their rooms; they're upstairs.

I clumsily hobbled to the second floor, found the two doors I needed. They were hard to confuse—on one, in large letters, was written "DO NOT ENTER," and on the other, a skull and crossbones like on a transformer was drawn. I turned the handle and went inside.

Unaccustomed, the cleaning took me quite a long time. All this clothing created unfamiliar sensations; the underwear constantly reminded me of itself, regularly digging into my butt—Damira gave me very minimalist panties, so if not for the belt, my cock would definitely have fallen out of them.

Periodically adjusting my clothes, I tidied up the girls' rooms. The mess here was excellent, as if they had been celebrating something over the weekend. Leftover takeout food was scattered everywhere, clothes were strewn about. While making the bed, I found a vibrator; it emitted that sweet womanly scent, causing the cock in the belt to tense up. Not knowing where to put it, I shoved it under the pillow. Damira's words wouldn't leave my head: "Be obedient, do everything you're told, and you'll be rewarded; if not, you'll be punished." What right do they have to punish me? Although for such money, I really am ready to do anything. Tuition for a paid education won't pay for itself.

— Mom, who is this? Our new maid? — shouted the short-haired one.

— Yes, Fatima, go, get acquainted.

In an instant, she was already next to me and began inspecting. The other girl was slowly coming up the stairs.

— O-oh, you're a boy, — Fatima was running her hands over my body, as if accidentally touching the belt. Mom said she'd find us a girl maid, but I think you'll do! — she slapped me loudly on the butt, making me jump.

— And what shall we call our maid, sister? — the second one had already approached and was examining me from a slight distance. The gaze of her cold green eyes slid over me, as if undressing me.

— Well, we need to think, what are those Russian names? Let her be Masha.

— That'll do, just right for her, — to say I was confused by how they addressed me is an understatement. — Hey, you, understand us? We don't care what your name was before out there; here your name is Masha or Maid.

I swallowed and, looking at the girls who had suddenly come very close, mumbled — yes, I understand.

— What did you say? Again? — The long-haired one approached and, putting her hand between my legs, squeezed my balls.

— I-I understand you, mistresses.

— Correct, we are your mistresses. Remember your place, maid. Let's go see how you cleaned up.

***