My Russell Hustle Pt. 04

As I said, all the fun went out of crossdressing. At least for a few days. I had two weeks to respond to Rene's deal.

As I went about my real estate business, meeting with clients and lenders, and showing a variety of sites, all the time with lingerie underneath, my usual smile was forced. But my business life went on. I kept wondering if these same clients would use me if the word got around about "Jessica" and her escapades.

Underneath, in my apartment at night, I still arrived home seething, swearing, and, well, sweating what dear Rene had brought down upon me.

Me, her maid! Fuck, she should be my maid! And if I bowed to her "program" for me, and let her own me, where would it all end? She had said she didn't want my money, but ..... she did eventually want me to buy us a home. So, that's extortion.

I really wanted to figure out a way to turn the tables on her and nail her for blackmail, but the media is always sniffing around for juicy sexual stories, and I am one of the top five commercial real estate agents in my city. She had me by the balls, or by my tits.

On the other hand, I still had a sexual thing for her. She was so pretty. But now I could kiss off her cute-shy-girl-next-door demeanor and see her for what she is -- a smart, conniving woman who's into power, just like someone else I know -- me.

I finally decided to squelch my womanly ego and give in to her -- just to see how things went, and perhaps find a way to out-think and outplay her over time.

I had really never cleaned house much. I grew up with well-off parents who hired maids (yes, maids!) to clean, and people to do landscaping. In college, in my apartment with two other guys, we did absolutely as little cleaning as possible (they never did know about my stash of lingerie). Upon graduating, after I went to work for a real estate group, it only took six months for me to start making enough money to hire maids. Five years later I had my own company.

My maids were usually young Hispanic women, and I made every effort to keep my feminine things all locked up and out of view. However, one time I mistakenly left my silicone breast forms in my sock drawer and I always wonder if they saw them.

I called Rene one evening.

"Hello Rene."

"Hello. I'll bet you are so mad at me."

"Yes."

"I was afraid you might get violent, but I'm glad to see you're reasonable about all of this."

"Not reasonable, but realistic."

Rene drew in her breath. "So, did you decide?"

"I'm going to give in to you, as stupid as that makes me feel. You know, I have maids clean my apartment here, and I don't look forward to being a maid to someone else."

"That's actually kind of funny," said Rene, now with a more sophisticated and mature laugh. "I want you to start the weekend after next. On Saturday."

"Well, actually, it would have to be a week later, because I have social commitments on that Saturday."

"Sorry, Jessica. It will be the day I specified. Cancel your commitments, dear. You will arrive at 9:30 Saturday, and I'll have your new uniform ready for you. I'll need your dress size. Bring your own lingerie, pantyhose and short-heel shoes, and short wig. You will sleep over, and complete your work by noon on Sunday. That afternoon will be reserved for some fun, if you're inclined to see it that way!"

I arrived on time, not wanting to tick her off and make things worse (how did I ever get in this spot?). I parked my BMW, walked in wearing a nondescript dress and shoes, and was met by a confident and smiling Rene, decked out in tight leather trousers, form-fitting summer top clinging to her boobs, wig pulled back into a business-like bun, and with Wall Street-like squarish eyeglasses. Completing the picture were reddish stiletto high heels.

"Welcome to your first day!" she exclaimed brightly. "I know we're going to have such a wonderful relationship. Don't you think so, maid Jessica?"

"I will try," I managed. "This is all new to me, you know."

"It just requires diligence and a work ethic," she pronounced. "Today, I will guide you through the proper procedures, what tools and cleaners to use, and what I expect for results. I will brook no complaints, snide remarks or unauthorized breaks. If all goes well, you will sleep in a bed tonight."

She ushered me into her bedroom where a black maid's outfit lay spread out on her bed. She left, ordering me to put it on, along with a maid's lace hairband.

Well, this was certainly some new aspect of my crossdressing career. Playing a fricking maid.

I felt the dress's satiny material, and felt, despite my initial negativity, a slight tingle as I slithered into it after dropping my own dress to the floor. I looked at myself in her full-length mirror. This had to be the German or Swiss take on a sexy maid's outfit: a white midriff made tighter by lacing, topped by a somewhat loose bosom, which my boobs filled nicely. The black skirt came to just below my knees, and the sleeves (ending in lace) came to my elbows. The dark pumps, pantyhose and bra and panties I'd arrived in, completed the picture. Except for one thing -- the back of the dress needed to be zipped up.

So I found Rene and politely asked her to take care of it.

"How did you address me?" she asked.

"Rene."

"That will no longer do. You will call me mistress from now on. That, or Misstress Rene. Understand?"

"Yes. I mean, yes, mistress."

"Good. And now I have a list of chores for you to complete today, dear." She handed me a neatly printed-out list of 10 or so things. "When you have completed these duties, and I'm satisfied, we will make dinner together."

With that, she zipped me up and tightened the lacing in front authoritatively. There was no doubt who was in control.

And, odd as it may sound, I no longer saw any vestige of Russell in her. She was thoroughly, completely Mistress Rene. Wearing tight leather trousers.

"So, you pass inspection dressed as my maid. Very good."

My first job was doing laundry. There were three washer loads to do, including her lingerie. So here I was, now a lowly maid. I didn't like the work, but I kind of liked being dressed as a maid!

While doing that, I multi-tasked and dusted, swept and vacuumed, with needed guidance from her. She was mostly watching TV or reading while I did this, hardly glancing at me, just like I hardly ever glanced at my own maids as they worked in my apartment.

Then came the bathrooms. Her written directions were very specific: clean out the toilet bowls and sinks with disinfectant, wipe down the outsides of the commodes, clean scum off the shower stall, clean the mirror and the surfaces around the sinks. Then arrange all her beauty products, drug store items, hand creams and more, in a neat fashion. This was really getting to be work, and it was damned demeaning. I was beginning to sweat and feel tired.

At one point, when I was having problems reaching to clean behind the commode, I was ready to chuck it all and quit. I quietly cursed. Do this every weekend? Shit!

But I pushed through as the loyal, industrious and energetic maid Jessica.

I ended my chores by emptying the dishwasher and filling it, cleaning the kitchen counters and mopping the floor. All this time, I really did feel like a female maid. Trying to make my employer happy with my job.

So unlike my carefree past!

It was 5 p.m. when I reported to Rene, I mean Mistress Rene, that I had completed my tasks. We did a walkthrough, and at every site, I was either complimented or criticized. More often criticized.

"This is your first day, Jessica, so I'll give you a bit of a break. But next time, of course you'll do better, won't you?"

Imagine, a woman 15 years younger than me talking down to me like this!

"I'll do better, Mistress."

"Good. Now you will help me prepare dinner. You can start by shredding some carrots for salad."

Standing next to her, I could almost feel her body radiating heat, as I looked at her nicely formed lips, nice butt in leather, and perfect boobs.

I wondered if in her past, she'd had another maid like me. She certainly seemed comfortable orchestrating me and putting me in my place.

Next she had me get various ingredients as she prepared a stir-fry dish using a wok, and had me set her table. She was to sit at one end, with me at the other end, eight feet away. I poured wine as directed, and we had a delightful, if distanced, meal.

"I'm glad to see that you've taken to your role so well," she said in a businesslike manner. "How did it feel being in a maid's uniform and serving me?"

"Well, Mistress, I loved the choice of uniform; so nicely fitting. But I will admit that I am not used to cleaning roles, and that was tough. I supposed you have videotaped me doing all of that too?"

"Of course!" she laughed. "Of course. Maybe sometime I'll watch them to get my jollies off."

"But I will endeavor to serve you, Mistress, and make you happy and honor you as my superior," I bullshitted.

"Well, what a wonderful thing to say, Jessica, even though I don't believe one iota of it. But listen to your own words, and you could come around to that point, you know."

That night, Rene slept in her bedroom, while I slept in a small guest bedroom. I so wished we were having sex like we did before, but that wasn't to be, so I just beat off, and very quickly fell asleep in my nightie.

In the morning, Mistress had me (back in my tight maid's dress) prepare the breakfast under her tutelage: bacon and eggs, with English muffins, butter and jam, and coffee. Tell truth, I had hardly ever cooked anything for myself, either buying frozen stuff or eating out. But I did my best.

Rene, still wearing a nearly transparent and provocative nightie, gave me a little peck on the cheek as a thanks before handing me a new list of to-dos. I could hardly wait to see what work adventures I'd have for a half day. Yeah, sure.

I folded her clothing I'd laundered the day before, unloaded the dishwasher again, re-arranged her large bookcase (I found she had a thing for Italian history and cooking), cleaned out her car, made the beds, watered all her plants and ... well, you get the picture.

While I'd enjoyed dressing as her maid at first, after a while my bra straps dug into my shoulders and back and my pantyhose chaffed my midsection. Then my wig began to irritate my scalp.

At 11:30 I reported I'd finished (she was watching TV). She had changed into a slinky-white, tube-style dress with very cute earrings. As usual, her boobs and butt filled it out nicely. Her lipstick was darkish and kissable.

Again, we walked through all my projects as she dropped her tart comments. Following her around somewhat meekly, I couldn't keep my eyes off her body. And I knew she knew it.

Lunchtime rolled around, and I helped her as before. This was topped with some delicious red wine. She obviously had good taste in that regard.

Finally, as I sat at the far end of the table from her, feeling drowsy after the meal and wine, Rene smiled.

"Dear Jessica, I'm so happy our arrangement is working so well, and that you're not moaning or groaning. Your thoughts?"

"Mistress, I'm of two minds. One is that I enjoy playing the part of a maid and dressing like one. Such a fetching, nice-and-tight dress! But, on the other hand, this work is very tiring."

"Ah, finally a complaint!" Rene laughed an adult laugh. "But, my dear, you will grow used to it. This is your new role in life. From playboy to toilet princess!" Another laugh.

"But this afternoon, this afternoon, as you know ... you will serve me in entirely new ways ... which I hope you'll like."

"Yes. Yes, Mistress."

"So, go take a shower, and I've left some new things for you to wear, to further serve me! Then come into my bedroom."

After the shower, which I sorely needed, and feeling all fresh and renewed, I went to check out my new outfit.

She had bought for me (how could she afford these things?) some tight, patterned leggings that I must admit looked sexy on me. For my upper, there was a white balconette lace bra with the sexiest cups. The breast forms were already inside. For shoes, there were some leather lace-up sandals; for earrings, simple pearls for my pierced ears. Finally, a blonde pageboy wig.

It was rather enjoyable having someone else dress me, especially since all the sizes were perfect and Rene's taste was impeccable.

I tell you, this woman was doing things to my mind .... Subtly.

Before I left I noticed a note telling me to put a dab or two of a provided perfume behind my ears. It was, I noticed, a rather expensive brand.

I entered her bedroom, taut with excitement and uncertainty. She was lying there, reading a book wearing those squarish eyeglasses again. Lying next to her was a whip.

"I've been looking forward to this, dear," she said in a somewhat coquettish voice. "And oh my gosh, look at you .... Do you like what I found for you?"

"Absolutely, Mistress. You have such great taste. I feel rather sexy, tell the truth."

"And the wig -- sets the perfect scene for me, really. I'm rather horny myself."

I didn't dare ask what the whip was for, nor did she mention it. So, I just stood there, waiting for further instructions. I loved the rise of my two bra cups, my boobs, above my chest.

"Jessica, do you like what you see?" she asked as she hiked up her slinky white dress so I could see her wonderful stretch lace panty, with the definite impression made by an erect cock underneath. There was also an unmistakable wet spot. I liked that.

"Of course. Of course, Mistress."

She deftly pushed her panty aside so her cock could spring erect.

"Come over and hold my lovely boi-clit, dear."

I gingerly sat beside her and oblidged. "Now, pull my pre-cum down my shaft, very slowly. Very slowly. That's right, very slowly."

She was watching me intently. I could only look at her gorgeous cock, so nicely erect.

"Mistress, could I ..... "

"Yes, you could, but only the tip."

My lips encircled the head of her wet penis. Perfect!