Maid For a Summer Pt. 01

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A young man discovers that the house he is looking after has a stern but beautiful maid living there as well. She pushes him to submit to chastity, a plug, and training.

No AI used at any point in the creation of this story.

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Maid For a Summer Pt. 01

I had a bit of trouble figuring out which key unlocked his front door, but once inside I felt calm and happy. Dumping my luggage in the living room, I flopped on the sofa. The red wallpaper wouldn't have been my first choice, but my friend always had strange tastes. He was off on the other side of the world "finding his truth", and I jumped at the chance to house-sit for a summer. The sun, the privacy, and the large luxury manor filled me with contentment, and I smiled as I stared at the strange artwork on the walls.

A distant droning noise upstairs interrupted my reverie. I thought I was alone? It sounded like it was coming from upstairs, so I located the staircase and tentatively crept up. I traced the noise to a room, and plucked up the courage to open the door.

"Take your shoes off!"

Inside was a woman vigorously pushing a vacuum cleaner back and forth, who didn't stop cleaning to shout at me again.

"You're getting mud everywhere. Take them off and put them by the front door."

My mind froze. I didn't expect anyone to be here, let alone to be yelled at for doing something wrong. And as an added distraction, she was beautiful. A bit older than me, with a strong-featured face. Her hair was tied up and messy, and a film of sweat made her skin shine. Long legs in black tights caught my eye, and I think she noticed me staring. I managed to stammer a response.

"I'm sorry, I didn't know anyone else was here"

"Your friend asked me to carry on keeping the house tidy over the summer. He said he wanted you to just relax."

I felt anything but relaxed. But then a thought popped into my head: Me and her, alone in the house for the summer, anything could happen... My flirting game was never strong, but I attempted to be suave.

"I'm glad you're here. Maybe you could come and relax with me once you're finished?"

"Don't try that on me. I see what type of boy you are. I'm going to finish my duties, and then I'm going to my room by myself."

That was pretty unequivocal. I muttered a response and made my way out, making sure to take my shoes off first. Looking round the rooms, I picked a nice one, but the biggest one was already taken by the woman. Exhausted from travelling, I had a quick shower and got into bed, trying not to think too much about her.

The next morning I came down to breakfast, which had already been prepared. The woman served it to me with a cold air. Surely I could now patch up any offence from last night.

"Thank you so much for the food! By the way, I never got your name?"

"It's Esther", she replied concisely, not asking me my name.

"That's a nice name. Are you working long today?"

"Yes. There is a lot of work to do around here. And I am the only one doing it."

Although I knew she was being rude, I've never been good at dealing with rude people. Making one last attempt, I asked her how long she had worked here, and she told me it was none of my business.

I passed the day away watching TV and swimming in the pool, with the woman seemingly always around, up until she retired to her room. In the evening I decided to get a bit free. I had always been into crossdressing, and this room I had chosen was full of women's clothes -- my friends partner. There was some nice pieces, panties with frilly lace and tight dresses. I helped myself, and masturbated with wild thoughts. Putting the clothes back in the drawers, I reassured myself that this would just be a bit of harmless fun for the summer. I would be proven very wrong.

Days passed, and I was pleased that the woman was being nicer to me now, even bordering on flirtatious. She must have just taken a while to warm up to me, and I didn't hold any grudges. One night we even sat together on the sofa, watching some documentary about ancient landmarks. She inched closer to me and I felt the tension, our faces were so very close. She said something that made me look at her, and we locked eyes and leant into a quick kiss. Her soft lips overloaded my mind, but she remained composed. Rubbing my thigh sensuously, she whispered to me.

"You know, I like guys who are into their feminine side."

Where did this come from? My heart started pounding. She continued.

"You're into that, aren't you? I know you've been having little dress up sessions upstairs. Nothing escapes me in this house."

I nodded meekly, but didn't say anything.

"I like guys who can commit to their feminine side. Can you commit?"

Not sure what she meant, I nodded once more. All I wanted was more of her attention.

"I would love if you could do something special for me. I've been wanting to try this 'sex toy' out on someone." She reached past me into a small drawer and pulled out a pink plastic object, displaying it in front of me and speaking in a sultry voice again.

"Do you want to try this with me? I know you will love it."

Was that what I thought it was? It looked like a chastity cage, like I had seen on some websites before. But I didn't care what it was, this gorgeous woman wanted to do something kinky with me, and I was never going to refuse. My defences were lowered. I nodded once more in agreement.

She grinned, and wasted no time in pulling down my jeans to reveal my smallish sized cock. With eager hands, she pulled the ring over my balls, and locked the cage into place over my penis. It was tight, and well and truly trapped in there. There was no sign of a key, but in that moment I didn't care. Her touch drove me crazy, and I started to get hard -- Or I would have, if the cage didn't prevent it. This seemed to delight her.

"So it works! I've always wanted to try a cage on someone, but my boyfriend didn't wanna know. This is so exciting!"

She had never mentioned her boyfriend before. I tugged and adjusted the cage, but it sat snug and firm. Suddenly, she got up from the sofa and stretched her arms up, revealing her midriff.

"I'm gonna shoot up to bed. I'll see you tomorrow, pet", she cooed as she walked out the door.

I was left dumbstruck, my encased cock still out, and the documentary still rolling on the TV. Not sure what else to do, I went to my room and tried to get as good a sleep as I could, my mind racing and body surging.

***

Sunlight in the morning woke me, and I wondered if my memories were from a dream. Reaching down to my cage confirmed its reality. I went to the bathroom, having to sit down. It surprised me how easily I adapted to this new device. On the landing Esther's door was still shut, which was curious, as she was normally up to make me breakfast.

On the kitchen island downstairs was a note:

'breakfast in bed pls. Cereal + coffee -- E xxx'

I assumed this was just more flirting, so obliged, making the cereal I knew she liked and brewing some coffee. The wooden stairs creaked as I carried it carefully up to her bedroom. Inside she was sat up in bed with the duvet down at her hips, and my eyes were instantly drawn to her body. A sheer silk nightie delicately draped over her perfect breasts, her nipples visible underneath. The sight of this caused me to freeze in the doorway, until her voice snapped me out of it.

"Excuse me. My breakfast?"

"Sorry Esther, here you go", I said handing the tray to her, not being able to draw my eyes away from her beauty.

"You can go now, pet" she said matter-of-factly.

Withdrawing from the room, I tried to collect my thoughts. Was she attracted to me? She kissed me, and dresses sexy in front of me, but acts so cold. Why would she want to use this sex toy cage of hers if she didn't want to do more? I grappled with the questions as I tried to relax that day.

The next few days were the same. A note in the morning, making her breakfast, admiring her body but being treated like a stranger once more. I couldn't make sense of whether she liked me or not. And to top it off, I was getting hornier than ever due to the cage stopping me masturbating. I was still dressing femme in the evenings, more often than ever. She knew now, so what did it matter?

One morning, as I served her her breakfast, she pointed to a large, overstuffed chair on the other side of the room.

"I've got a fun change, pet. That's your new outfit to serve me in the morning."

The outfit in question was unmistakeably a maid's outfit. Not a costume, like some cheap Halloween piece, but a quality outfit. Black cotton was overlaid by dainty white material, and a detachable apron. A network of lace tightened the garment at the back, and a matching headband lay beside it.

"I can't wear that around the house!" I exclaimed, "what if someone comes round?"

"Oh, whose coming round? It's just you and me here. I like boys who can commit to their femininity, remember. But if you don't want to take the next step with me, that's fine."

As she said this she stretched, pushing her breasts forward and letting the duvet slip down to reveal her stomach and a flash of her panties, before she coyly pulled it back up. She knew how to manipulate me. I would agree to anything that got me closer to her. Delicately, I scooped up the outfit and left her room without saying another word.

Another morning, another erection prevented by the cage. I could feel myself getting more pent up by the day, and dreamed of the day when our sexy games will come to a climax, and I can be with her fully. All my actions were to accomplish this. I put the maid outfit on, and checked myself in the mirror. I looked good, my naturally feminine hips accentuated by the tight fabric. I decided to add a pair of heels I found in the bedroom. The skirt was short, short enough that my cage could just be glimpsed if I moved in the right way. I headed downstairs.

The note this morning was a bit different:

"Usual breakfast. Hoover 1st floor. Dust all artworks. Clean oven. Bring me glass of merlot in living room 17:00 -E xx"

I gingerly brought this up as I handed her the tray of food in bed. To tell the truth, as attracted as I was to her, I was a bit intimidated by her. Her response was characteristically straightforward.

"You're dressed as a femme little maid aren't you? Don't you think you should be living the part? Without service, you are just someone playing dress up with a cage on their cock."

I blushed at this comment, which to her was like blood to a shark.

"Furthermore, you are to stop ogling my body. I thought the cage would prevent your incessant salivating over me, but it seems I need to lay down the law. After all, my boyfriend wouldn't be very happy with you if he knew you were staring at my breasts every day."

"Hey, that's not -"

"Don't interrupt!" she yelled. "You obviously need more training. If you are a good girl for me, then I will think about letting you out of the cage for a while." At this she fiddled with her necklace, which upon closer inspection I realised was a key on a silver chain -- the key to my chastity cage. The key sat on her smooth skin, between her beautiful breasts. She glared at me, and I remembered her order, averting my gaze to the floor shamefully. I was so overwhelmed I didn't even have time to process the fact that she called me a girl.

"You can go now, pet. I expect everything on my list to be completed today."

It had become common that I would leave her room in the morning feeling dazed. The only thing to keep my mind focussed was to follow her commands. I got to work cleaning the house, my embarrassment countered by the horniness causing my cock to swell against its confines. She didn't seem to do any work that day, but would occasionally pass me by, telling me that I'm doing a good job.

Just before 5pm I got the glass of red wine ready, and carried it through to the living room on a serving tray. She was listening to calm music in too-revealing pyjamas that clung to her thighs.

"Thank you pet, you've been ever so good today. You've really taken to your role. I'm proud of you." Taking a sip of wine, she looked me over and allowed the rare compliment to sink in and take effect. "Do you feel happy?"

"I think so, Esther" I replied cautiously. Even when she was being nice, she still scared me.

"That's grand. But Esther is what my boyfriend calls me. Given your situation, I think you should call me mistress from now on. How does that sound?" Again, she toyed with my key, her key, to remind me of my place. Any hope of being released rested on satisfying her.

"That sounds OK, mistress."

"Good. Very good. Now there's another thing I would like us to try together. Are you interested?"

Of course, I nodded obediently, and waited.

"Fabulous. Have a look in that box over there, pet."

I picked up the box she referred to and pried open the cardboard lid. The object was covered in styrofoam, which I peeled off and placed on the coffee table. I recognised the object -- It was a big, black, butt plug. Although I had heard of them, I'd never seen one in the flesh before, or tried anything similar. It felt so heavy. She let me look at it, then carried on talking.

"It's another toy I want us to explore together. It would be so hot to me if you would wear this around the house. I'd love to see you so committed to being feminine for me. But it's up to you. Take it to your room. Goodnight, sweetheart."

I had learnt to leave promptly when she told me too. Back in my room, I sat staring at the plug on my bed. Surely this is too much, I thought. But I had come this far already, what was one more thing... And my horniness had got me not thinking straight. Of course I had considered playing around down there before, even seen some porn featuring it... It was my only chance at release. I had to give it a go.

I woke up early, grabbed some leftover lube in the bathroom, and decided to give it a go at least. I tried sliding the plug in. It was big, and it hurt at first, but eventually I got the widest part in and the whole thing popped inside, making me gasp. My muscles contracted in waves and my body contorted to accommodate the new object. Touching a finger to my cage, I pulled back a sticky droplet of precum that had been forced out, representing weeks of frustration.

It felt too foreign. Invasive. I resolved to remove it as soon as my body relaxed, when suddenly my door swung open without warning and Mistress Esther strutted in, triumphantly calling to me.

"My my, you don't waste any time do you. I knew you were a little slut deep down."

"I was just trying it Mistress, I'm going to take it out."

"But you haven't even felt the best bit yet."

I looked at her confused, as she pulled a device out that looked like a small TV remote. With a smirk and the press of a button, my plug jumped to life. Vibrations pulsed through me, focussed entirely on my most sensitive spot inside me. I fell to my knees on the bathmat. I hadn't felt physical pleasure like this in what felt like a lifetime. My brain fogged over and my cock jumped, leaking even more precum. Then, just as suddenly as it started, the vibrations stopped.

"I'm glad you like it", she said arrogantly. "But I guess if you don't want the plug, I'll take it back then."

"NO -- I mean er, that's okay Mistress, I will keep the plug in, if it's important to you."

I was trying to maintain any shred of dignity I had left, without giving up the ecstatic feeling I just experienced. She just smiled again.

"I thought you would. Good girl." Upon saying this last remark she tapped the remote again, sending another short pulse of pleasure through me. If this makes me a good girl, then I want to be as good as I can for her.

***

My days from then consisted of cleaning, attending on Mistress, and feeling frustration in my room at night. I couldn't masturbate. I couldn't order any sex toys online, as Mistress managed all the post. The plug was too wide to do anything but sit stationary inside me. I couldn't even use the vibrations myself, as they were controlled by Mistress. And control them she did.

When I did something that pleased her, she would tap her device and send a pulse of movement into me. She would always pair this with verbal encouragement, calling me her 'good girl, her docile servant'. One morning I picked some wildflowers to serve with her breakfast, which pleased her so much she set the vibrations to max for a good twenty seconds. It was never enough to cum, but enough to make me hungry for more. I looked for any way possible to satisfy her. Part of my brain always held out hope that she would unlock me, but another part of me only wanted arousal from other means.

One day, Mistress had been exercising in the home gym while I cleaned the dishes. I anxiously kept an eye out for when she was done, so I could promptly bring her her towel. She liked that. But today she came in to the living room and plonked on the sofa, sweat beading down her forehead. I trotted in to give her the towel, which she took with a soft pat on my bum. Mistress had changed my maid outfit for an even shorter one, for 'easier access'.

"Good girl."

Whenever she said this my genitals twitched, in anticipation of stimulation that may or may not arrive. She tapped her remote, giving me a shot of the vibration I craved. I was being conditioned like a dog, but I didn't care. She thought I was a good girl.

It was difficult, but I tried not to look at her body. She was wearing tight gym gear, that only just covered her boobs and crotch. I could smell her scent, and it drove me wild. In the few glances I took, her toned core and sweaty thighs inflamed me, but as always my energy had nowhere to go. I waited obediently in silence.

"You've been such a good girl for me recently. I think you deserve a little treat. Would you like that?"

"Yes please, mistress", I said shyly, not knowing what she had in store.

"Put these on. Hands behind your back. Kneel on the floor."

She chucked a pair of fluffy pink handcuffs at me. I did as she told me, and knelt in front of her on the sofa. Then, she did something unexpected -- she took off her gym shorts, chucked them away, and spread her legs to reveal her full crotch to me. I had never seen it before. It was neat, with close shaven pubes, and was as sweaty as the rest of her. With two fingers she spread her labia, revealing the rosy flesh underneath. My eyes were transfixed. Her fingers caressed her clit, before slowly sliding inside her wet pussy, causing my cock to strain as hard as it could in its cage. She reached her fingers towards me.

"Open for me." She said, and I opened my mouth, accepting her fingers slick with her wetness, which pushed down on my tongue.

"This pussy is your ruler, do you understand? Everything you have done since entering this house was for this pussy. Even that cage on your cock and plug in your ass was because you are weak in front of my womanhood. But you will never fuck me. My boyfriend does the fucking. All you can do is serve me. Make me happy, in the hopes that I might give you a crumb of relief. It's a beautiful thing, that you have realised your purpose is to make others happy. I knew it was your nature from the moment I saw you."

She continued, "Now pet, your reward. You get to lick me, while your cock stays safely locked. I'll even turn the vibrations on in your little plug, because I'm feeling generous. Get to it."

Her hand moved from my mouth to her remote and my plug powerfully hummed.

I had gotten exactly what I wanted all this time -- Her legs open before me, asking me to touch her. But I hadn't expected it to be like this. She was even more intimidating like this, spread proudly, awaiting my service. I felt honoured that I was invited to make her happy, but scared to touch her in that holy place. Scared, but safe at the same time, secure in my cage and my submission to her.