A Maid Man

by Patricia Violet

 

Chapter 1: The Arrival of the Delicate Miss Wilkons

Ashton was a struggling author, but he could never seem to stay focused on a story long enough to finish it. So one summer after many failed attempts to write his novel, he moved out of his apartment in Manhattan to his family's small summer cottage out on a small lake upstate. Out here he could focus on writing and nothing else, or so he thought.

He called my residence looking for my grandmother, who had kept house for his family up at the cottage for years. I told him that she had passed away last winter, but that he need not worry because I would gladly take her spot until he could find a suitable replacement when I went back to college in the fall.

My name is Maria Bordeaux. The summer that Mr. Wilkons, Ashton, Ashley, or whatever you would like to call him, stayed at the cottage and I kept house for him. I was 21 years old. I was a student at NYU majoring in English and thinking about law school. I came from a poorer family, but I was smart enough to grab a lot of the available scholarship and grant dollars. I was hoping that Ashton would pay me big for cleaning for him. Well...let's just say it sure paid off all right!

The day he arrived at the cottage I had already been there fixing it up for him for a week. When he pulled up and I went out to help him with his bags,I was wearing a small black French maid's getup that showed off my deliciously long legs in their sheer black hose. I figured a little sex appeal couldn't hurt my earnings. I ended up doing a lot more than that!

Ashton got out of his car and couldn't help but look me up and down for a whole two minutes before I finally broke the silence. I said, "My name is Maria Bordeaux," and lifted my short skirt and petticoat in a little curtsy. "Pleased to meet you."

"H-h-ello, I'm Ashton. Ashton Wilkons," he stuttered in response. I asked if I could help him with his luggage. He refused and hurried to haul all of his bags into the house at once, so I wouldn't be able to help. He ended up dropping three of them. I followed, picking each one up as he dropped them. By the time we were in his bedroom, he was setting down the two bags he was struggling with as I leisurely dropped the three I carried on the bed.

He was a terribly pale and skinny man, but not entirely unattractive. He had the soft features of a bookworm who didn't get much sun. I always had a thing for the cuter dorks like him in high school. Even though he was nearing thirty, I felt this same attraction for him. So each day I continued to wear my sexy little French maid outfits, and I am sure this kept him stiff as a board every time our paths crossed in the little cottage. Soon I would control every aspect of his life.

His face reddened when he saw me throw down the three big bags I had handled with such ease. My body was tight and slender from frequent workouts and lots of housework, and even though I was short (5' 3"), I could tell that I carried more muscle mass on my bones than this rag doll. Judging from the redness of his face, he knew that too. "Uhh, thanks," he mumbled to me.

"Anytime, Miss Wilkons, ahem, Mr.Wilkons." I answered as I curtsied again and grinned at him. "You can call me anytime you need anything heavy carried or a tight jar or something opened," I teased, and walked out of the room, leaving him to watch my tight butt wiggle away in his embarrassment.

 

Chapter 2: Maria's Offer

Over the next few days, I got the idea that Ashton was avoiding me. Every time I entered the room he was occupying to clean up or dust, he would quickly ramble off some absurd excuse and hurry away. I did manage to trap him in the parlor and embarrass him once more during that first week, which was the only week of the summer that I cooked and cleaned the house for him.

He was sitting in a recliner reading and listening to the radio by the fire in his robe. I kept using the excuse that I was so behind on housework and that's why I kept staying at the cottage late into the evenings, but I was really just feeling him out before I set my trap. I offered him a cold beer. He said sure and thanked me when I brought it to him. I also grabbed one for myself, knowing he didn't have the gall to question me about drinking while I was working. He struggled to open it and failed. "Maria, I think these aren't twist off caps. We need to get the opener."

"Nonsense,"I said as I opened mine easily. "Let me have a try at yours, hun," I said, and grabbed it off him. I opened his with just as much ease as mine, then gave it back to him. "There you go, you must've loosened it up for me," I said as condescendingly as possible, with a giggle and a wink.

"Thanks," was all he said, and his face reddened with shame once again. He didn't know it, but the beers did need to be opened with an opener, which I had concealed in my maid's apron pocket and was using with a quick flick of the wrist, too quick for Ashton to notice. I was thoroughly enjoying humiliating him, so I thought it was about time to advance the plan a little further.

"How's the writing going, Miss Wilkons, cough, sorry. Mr. Wilkons," I asked, innocently enough though the grin never left my face.

"Umm, alright." He was terrified of me. This was good.

I walked around his chair, set my beer on the end table,and placed my hands on his shoulders."What are you writing about? It's not a romance is it? I just love those romances. All those lovely descriptions of the throes of passion. Oohhh," I cooed to him.

He winced and dropped the newspaper he was reading as my hands worked into his shoulder muscles. "Ahhh....no, it's actually a story about a man who leaves his hometown to go to war." He gasped it all out in stressed syllables, but seemed to gain confidence at the mention of his work. Time to get the ball back...his balls.

"Oh," I said and quickly withdrew my hands from his body. "I don't

like nasty books about violence," I said disapprovingly. I picked

up one of his dainty, girly hands and spoke again. "And quite

frankly, I can't see a delicate and sensitive man like yourself

writing about such terrible things"

"Sorry," he said, "but that's what it's about and I'm really quite proud of it."

"Oh really?" I asked with a raised eyebrow. "If you're so proud of it, I want to read it."

"Ahh, but it's not finished yet Maria, and I only have about ten pages written so far...." He was trying to escape but I wouldn't let him. After some more arguing, I broke him down, and he finally got up and went to go get his manuscript.

When he returned, I was sitting in his chair. I patted my lap. "Come sit here and read it to me." He did. It wasn't that bad, but it didn't seem at all natural to me. I couldn't believe Ashton, who had only read about war, was writing a soldier's account, and I told him so. I suggested I go grab one of my trashy romance novels (which actually had belonged to my grandmother—I enjoy more intellectual or philosophical literature), and I read it to him to see if he'd rather write about that stuff.

He refused at first, but I pushed on with my expert powers of persuasion. "But Mr. Wilkons," I whined, "I could sit here every night on your lap and read to you like you just did to me and it would be so nice and inspiring for you own romance stories, too."

He couldn't help himself. Like all men, his sex drive overrode all reason. At least in that one aspect he was like a man. "I guess we could try it out tonight Maria, and see how it goes." I pretended to coo with glee and hugged him tight and then ran to grab one of my grandma's books. Before going back to my little toy, I found a place where there was a graphic sex scene being described and marked it with a bookmark. When I got back, I lifted up my skirt and petticoat so that my silk black panties were directly on top of his body. I squirmed until the middle of my butt nestled over his robed erection.

"We'll just start where I last left off. I'm sure you'll be able catch up, okay?" I didn't wait for an answer and opened the book and began reading of the "caressing" and "throbbing". As the book got more and more intense I began to rock my hips and create friction with my panties on the erection inside his robe, the whole time bopping my head and pretending I was feeling the music on the radio. He reached for the radio to turn it off, obviously close to losing control over heat in his groin. I smacked his hand away playfully and paused from my reading to tell him, "Oh no you don't. I love this song." I resumed reading and rocking my hips as I described the steamy sex scene in the book. Eventually, I felt dampness against my panties. I shot up in pretend surprise. "Oh my," I squealed. "I was right. You really DO enjoy these types of books."

Ashton just sat there redder than ever. He stammered an attempt to speak but eventually closed his mouth again without forming any words.

I picked up again. "Well now we at least know what kind of book you should be writing. I want to read more of it once you settle into your natural style. Perhaps the soldier could fall in love with a nurse after he is wounded in battle. Or...," I paused and smiled at this next thought, "with one of his own platoon. Is that more your taste, because you know, most men don't read these books. But then again, most men aren't as delicate and soft as you are."

He sat there stunned and dazed. "Tell you what," I said. I was now dictating his actions to him. He nodded at me, showing he understood and he would do as suggested by me. "You look tired, so get to bed and I'll clean myself up and then do the same. Tomorrow night you can pick out a new romance for us to start together and I'll read it to you every night. I'll start sleeping here too in the other bedroom, so we can read later into the night. Of course I'll be getting paid, because it's all to help you write that novel." He nodded every time and muttered "yes's" and "of course's" to everything. "Alright, everything's settled then."

I curtsied again and walked to the other bedroom. "G'night Miss Wilkons." As I left him there alone in the parlor, I did not take the time to correct myself this time.

 

Chapter 3: Hugo And Josie

So I read the trashy romance novel to him every night for the rest of the week. Rocking my hips on his erections until he would cum for me. Then, I would pull out a hankerchef and dab up his cum for him.

On the fifth night, I took one more step in my plan to bring the ever so soft Ashton to my mercy. "Ashton," I began innocently. "Tonight could we act out the book instead of just reading it. I used to touch myself while I read them, but now I'm too busy helping you with your book to enjoy them that way."

He couldn't believe his ears. "Sure, Maria, whatever you want," he said, unable to stop a goofy grin from spreading across his face.

I smiled at this. "Good, that's EXACTLY what I wanted to hear." I opened up where we left off and started acting out the part of Hugo, the sexy, masculine love interest.

He was actually man enough to protest at playing the part of the book's young and naive heroine Josie, at first. How cute! "Maria, wouldn't it make more sense if I acted Hugo's part and you were Josie?" I just stared at him looking at him as if he had just said something very ridiculous.

"Why would we do that?" I asked.

"Well, you know because....umm....I'm a man and you're a woman......"

"Oh," I said as if suddenly enlightened. "We COULD do that, but you know, mostly women buy romance novels. In fact you're the ONLY man I know who enjoys them. It could help you get into the character so you can accurately write about a woman's feelings. Or else your readers will see right through you."

He still seemed wary of the idea, so I pushed on. "It's not like there's anything wrong with being a woman, Ashton." I said this gruffly and put my hands on my hips. "And besides, I think personality-wise I'm a much better match for Hugo. An you're a perfectly delicate Josie, don't you think?"

I waited for his response. And got it what I wanted. "Yes," he mumbled.

"Yes, what?" I asked innocently as if I had suddenly lost the thread of conversation.

Yes, you're right," he answered me, very red in the face.

"Right about what," I asked. This time letting him know I was being coy and wanted to hear him humiliate himself. He was hopeless to "act" out the sexual parts of the book with me, and folded.

"I would make a better Josie and you would make a better Hugo." He hung his head in shame.

"That's a great idea!" I said. Before he could object further, I went on with the acting. I had patiently waited for us to reach this part of the book. It was the part where Josie finally got down on her knees to satisfy Hugo. It was also filled with plenty of ass-grabbing and copping of feels, all at naive little Josie's expense.

I put Ashton through every torturous molestation and often made him repeat Josie's lines until he said them in a soft, feminine drawl that satisfied me and convinced me that he was "feeling the woman's role adequately". I especially enjoyed it when I made him say the line, "Hugo, I've never felt more like a real women then I do when you touch me under my skirt," over and over again in his best Southern belle imitation, while I stroked and teased his genitals.

Finally I uttered the line I had been waiting for, "Then, Josie dropped out of Hugo's arms and to her knees. She undid his belt and button and unzipped his fly with her teeth." I looked at Ashton expectantly and with an arched eyebrow as I held him in my arms. "Ahem, Josie."

He dropped to his knees. He reached under my skirt to pull down my panties, but I smacked his hand aside playfully and reiterated, "unzipped her fly with his teeth." Ashton took the waistband of my black, French panties in his mouth and slowly pulled them down around my thighs.

"Josie then took all nine inches of Hugo into her mouth. She wrapped her luscious lips around his throbbing organ and ran her tongue up and down his shaft and over his head, tasting the beginning of his juices." I read on a few more moments as Ashton probed his tongue into the moist folds of my cunt. He was cautious at first, but soon was vigoriously slurping up every drop of my wet pussy. I dropped the book and collapsed into the recliner. With my thighs up on his shoulders and clamped around the sides of his head, I trapped Ashton in my pussy. He licked and sucked at my pussy and ran his tongue along my lips before pressing his tongue to my clit. I orgasmed after a couple minutes and he continued to run his tongue through the core of my womanhood. He kept at it and soon my excitement increased once more, and I clamped my thighs around him again. He continued sucking up every last drop of my juices as he licked and probed my pussy to a second wonderful orgasm.

That night I invited him to share my bed with me, once I'd cleaned myself up. When I told him it was ok for him to come into my room, I was already lying in the small twin-sized bed. He laid down next to me in his boxers. I was wearing a see-through baby blue babydoll with matching demi bra and thong panties. I made sure he got a good look at my ass and nipples as I let him under the covers. He complained that there wasn't enough room and suggested we move to his bedroom where he had a larger bed. I told him he could go, but that I was too tired and going to stay put. As an afterthought, I suggested that if curled up at the foot of my bed, he may have more room. Like the dog that he was, he complied and slept there.

Everything was running smoothly.

 

Chapter 4: The Education Of Miss Wilkons

I awoke him in the morning with a soft kick in the side. He stirred and sat up. I slid out from beneath the covers, still clad in my blue lingerie set, and sat down next to him at the foot of the bed. "I know we're not role playing right now, but I sure could use your services once more."

"What do you mean," Ashton asked me confusedly.

I snapped my fingers and pointed to the floor in front of me. "Oral services, Ashton!"

He responded quickly and eagerly, practically jumping off the bed and onto his knees in front of me. I lifted my nightie, slid my thong down, and spread my legs invitingly. Ashton pushed his tongue right in and started working my slick pussy. God, he must really love eating me out, I thought to myself!

As Ashton serviced me, I began to talk in what seemed an idle voice, but was actually the most crucial part of my plan for my little toy. "I took the liberty of reading the new part of your story that you wrote last night, I hope you don't mind. And while I must admit there was a lot of improvement, and I'm glad that you've taken my advice and made it a romance, I still don't think you truly grasp the female character. It comes off forced, but don't worry, I have the perfect solution for you. I know how to get you to truly get inside the head of a woman."

Ashton leaned back for a second, his lips wet with my juices.

"How?"

"Listen," I said and grabbed a his hair and pushed him back down on my wet cunt. I let out a moan as he resumed his work, and then went on with my plot. "Well, I decided that we could switch places for the remainder of the summer. You know, you could wait on me and cook for me and do the housework....and oh, of course, to get the total sense of womanhood, you'd dress the part."

At that he started to withdraw his tongue from me and protest, but I had anticipated this and clamped my thighs around his head, trapping him in my pussy. He had no choice but to keep working, and soon brought me to another delicious orgasm.

We sat there still for a few moments and then finally he broke the silence. "I'm not to sure about this....dressing like a woman and everything."

"What aren't you sure about," I began. "We already agreed last night that you'd make a better girl than I do, and hasn't your writing gotten better and your summer been more fun since you started taking my advice? If you're not sure, maybe what you really mean is that you've been using me, and you should find a new maid!" I said this with emotion and sold it a the end, complete with alligator tears in my eyes.

"No! Using you!? Come on Maria, you know its not like that at all!

I take it back, we'll do it your way!"

"Promise?" I asked with pouty lips. "Whatever I say, you'll do?"

"...yeah, anything..." Hook, line, and sinker, he was mine!

"Ok, then," I said with a complete change in my mood. I stood up and took Ashton by the hand. "Pick up that thong and follow me to the bathroom."

I took off my remaining clothes when we got into the bathroom, and stepped into the shower. I pulled Ashton in with me and turned on the water. I grabbed off a bottle of hair remover from the shelf and began to rub it liberally on Ashton's entire body. "This'll make your skin soft and silky, just like a real woman's. And Miss Wilkons wants to be as much like a real woman as she can possibly be, right?" I looked up at him expectantly for an answer.

"Of course," he said helplessly. I giggled, and his face reddened as he hung his head in shame. What shamed him even more, though, was the rock-hard erection he got when I applied the cream to his pubic area. I let the cream soak in for a few minutes then sprayed him off. I had him wash his hair with my floral scented shampoo and wash his body with my scented soap. When he was done, I ordered him to do the same for me. Again I noticed his throbbing erection. Like all real sissies, he enjoyed serving his Mistress. Now it was time to get serious.

We got out of the shower and dried off with fluffy pink towels, then I led him into my bedroom and opened up my top dresser drawer. I removed a pair of frilly, French-cut, pink panties. "These are yours now, angel," I said with a smile, and handed the undies to him. "Put them on."

He did as he was told, and slid my pantied up his thighs until they encased his cock, balls, and butt in a silk prison. I noticed his member yet again swell to attention. I knew he was a true sissy from day one. "Hehe, for all your protesting it sure looks like you enjoy playing the role of a lady." His face turned the color of his new panties. "Aww, it's ok Ashley, I understand. Come on over here and ask me to finish dressing you up."

"Will you finish dressing me up as a girl, Maria?"

"Of course, darling." I hugged him tight against me, his erection pressing against my naked pussy.

I took out a pair of plain, black panties for myself and slid them on. Then I threw a black dressing gown over top and concentrated on my newest girlfriend. "Let's get you in a garter. Take your panties off, sis."

"But I just put them on, shouldn't I..." he trailed off.

I sighed to show my disapproval. "Look, you said you'd do as I say, little lady. Now I don't have time for you to question everything I say. So do it the first time."

"Yes, Maria," he complied, and slid the silkies off his body, letting his hard cock stick straight out."

"Oh, and one more thing. Since we're switching places for now, that makes me your boss. So you will address me as Mistress Maria from now on. I shall call you whatever pleases me, and you will answer to it. Understand?"

"Yes."

"Yes, who?"

"Yes, Mistress Maria."

"Excellent," I said with a grin, and smacked Ashton playfully on his ass. "Now, to get you dressed..."

I chose a nice white garter belt with lots of lace and helped him correctly place it around his hips. Next, I found a pair of sheer white stockings with lacy tops for his legs. I showed him how to properly roll the nylons up into an "o" to ensure his stockings didn't get runs in them. Then, he pulled his pink panties back up his legs and snugly around his genitals for a second time. I wanted him to quickly get used to the feeling of delicate silk on this part of his body. I had him put on a white petticoat next, and then a short, pastel pink maid's dress on top of it. The dress ended at mid-thigh and frilled out from the short petticoat underneath it. I went to my closet and pulled out a pair of pink pumps with modest two-and-a-half inch heels. I had him slip these on his feet. As a finishing touch I wrapped a lacy, frilly apron around him, tied it in a big bow, and pinned a small maid's cap on his longish hair after I brushed and straightened it out.

I sat him down at the vanity and did some make-up work on him. I applied a layer of foundation, then added mascara, eye shadow, and eyeliner. I then had him apply some blush and bright pink lipstick to match his maid's dress and panties. The whole time I gave him tips and instruction, explaining that he would be doing this all by his sissy self starting tomorrow.

I led him over to the full-length mirror so he could see himself. "Now, Miss Wilkons, do a spin for me." I took his hand and lifted it up as he obediantly spun in a small circle, like a dancer. As he spun, his skirts flew up and I could see the lacy tops of his nylons. I ordered him to walk up and down in front of me in his new heels. I would increase their length as he got better. "Dear, take smaller steps and weave those hips more. Don't be a shy girl. Now, let's practice your curtsy."

He looked so soft and feminine; I truly admired the work I had done...

 

* * *

 

For the rest of the day, I took Ashton through the house, and we did all the housework and laundry together. I showed him how to properly handle our delicates, and kept making him promises to take him for a manicure or out for a perm or lingerie shopping if was a good little girl for me. He quickly and quite naturally lost all sense of his male self and gushed at these promises.

Starting the next day, though, I sat around and relaxed, as I ordered Aston, or Ashley as he was now constantly addressed, to do my bidding. She fell quite naturally into her new role, and continued to write her romance novel in the evenings. I also let her lick my pussy every evening before bed. I never touched her, and she was only permitted to touch herself if I pinned her ankles back towards her shoulders so she could ejaculate directly into her own mouth. Ashley enjoyed this, and I was forced to permit her such a pleasure only once a week as a reward for extra good behavior. Every once in awhile I'd take her out to town to do some clothes shopping, or for manicures or pedicures. Once I took her out to do some clothes shopping, boy, did that sissy go nuts! She ended up spending over two hundred dollars on lingerie alone.

 

 

Epilogue: A Maid Man Forever

By the end of the summer, Ashley had written a beautiful, trashy, romantic masterpice. At my command we published it under my name, and with its success I received a five-book deal with the publisher. I had Ashley sign over the deed to the summer cottage and we moved in there full time. With my income set, I quit school and did whatever I pleased all day. With the money from the contract I added on to the cottage until it was a small mansion on the lake. I continued to have fun with Ashley. She kept house all day and wrote my next book in the evening, if I didn't require her services.

With nothing to do, I often had dates over at the cottage. I'd "suggest" we bring my maid into the fun. At my cue, Ashey would strut out, now with quite a striking figure from her hormone therapy, and join in the fun. Often we would do double team blow jobs, or I'd have her suck his dick while I sat on his face. Once my date had left, I'd sit on my sissy's face and let her clean up both our juices. A couple times I even had my dates ram their cocks up her ass. Afterwards, I'd have to pin her legs back and let her cum into her mouth, sometimes twice in a row because she was so damn excited. Then I'd shove a tampon up her ass to stop any dripping. Since she seemed to enjoy this so much, for her "anniversary" I bought her a nine-inch dildo, which got much use on the nights I didn't require her for a threesome. Soon she also started wearing a vibrating butt-plug, which I held the control to as she went about her daily housework.

One night, about two years after her transformation, Ashley knelt at my feet after slurping up my juices and Brad's (my current man's) cum. Brad had also fucked Ashley's ass. Brad knew all about Ashley and loved her. He stroked her to orgasm as he rammed her from behind, and at my instruction, had her lick his fingers clean afterwards. Ashley knelt in front of me, now, with the long, kinky, night at it's end. She looked at me with tears in her eyes. "I just wanted to thank you for everything you've done for me Mistress Maria. I love you and the life you've given me." With that she burst into tears.

I cradled her up into my lap and soothed her. "It's ok Princess, I love you too. You're welcome to it all. Now come on, you've got to stop crying, so you can cum in your mouth before we get you off to bed....

 

THE END

  

  

  

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