Sissy's Revenge

Ok, My last post received quite a bit of negative responses because my protagonist was a total wimp and let his wife walk all over him. Well in this one, in the end, stands up for himself.

Warning: this story contains all the elements of cuckolding save one and feminization of males. If you have a problem with either of those, then quit reading here. Skip right to the end and tell me I'm a crappy writer and I write trash and shouldn't waste the bandwidth.

Synopsis:

OK, there are lots of stories on the web about guys who's wives decide that they'd rather have a girlfriend than a husband and secretly feed him hormones as they seduce him into being their sissies. These dopes seem to be totally ignorant and unable to figure out there's something wrong. But, what if the sissy is just a little smarter than the average sissy and what if he's just a little stronger willed then the average sissy and what if he checks things out with his doctor? What then? Read and find out.

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Prolog:

My Doctor found out about my cross-dressing. It wasn't like I had intended to tell her, but it was sort of hard not to, given the sequence of events. I had been trying to start my own online business while working full time at a 9-5. That meant 40 + hours there and 60+ at home. Needless to say, I hardly had time had time to sleep, let alone eat properly. Usually my diet consisted of as many raw calories I could stuff in while still working a keyboard and mouse to do research and cut deals with suppliers. Whatever I ate, was washed down with gallons of coffee and any other caffeine drink I could find, augmented by caffeine supplements. Can you say 'No Doze?' Or maybe, 'Wired?'

You could ask, just why was I so determined to get this business off the ground? Easy, have you've every looked at specialty shops that cater to cross-dressers. The prices are outrageous and the offerings are so garish that it makes you want to puke. I mean who needs six-inch platform heels when you're already on the tall side for a woman? Those kind of shoes would put me at over 6' 3". Now there's a woman who'd get noticed. My theory on dressing as a woman is simple. You want to look like a woman. Just your average house wife. It's a lot easier to pass if you don't stand out. I was determined to provide clothes for cross-dressers at the same prices as women buy them.

Well anyway, Lucille, my new wife, insisted I go to the doctor about my run down condition. Since I had given her my symptoms over the phone, the doctor drew some blood as soon as I came in. Her nurse took it somewhere. She then took the usual readings, blood pressure and pulse, listened to my heart and lungs. We talked about what I was doing. She'd ask a question, I'd answer, she'd nod and make a note. Just as I was sure we were done, the nurse brought in some paper work.

The doctor looked it over and said, "Just as I thought, with your eating habits. You have a vitamin deficiency and I'd guess you also have a sleep deficit." She turned to the nurse. "Prepare multi shot while I write a prescription." She went on to lecture me about taking better care of myself. She gave me a list of vitamins I should take and quantities. Then, as the nurse returned with a syringe, said, "OK, turn around and drop your pants. We'll get you started right."

Oops. I never considered I'd have to do anything like that. I had my red panties with black lace on. My face burned as I did as I was told. I tried to hook my panties with my thumbs to pull them down at the same times, but the doctor noticed my efforts.

"No need to pull your underwear down, you just hold your shirt out of the way. I'll take care of the underwear."

Well, she is a doctor and the Hippocratic oath forbade her from telling anyone about what she found out in the process of ministering to me. "Umm, nice," she said and plunged the hypo home.

Red faced, I pulled up my pants, "Look Doc, ah, I..."

"Don't worry about it, I see that kind of thing all the time. You'd be surprised just who, if I could tell you. Your secret is safe here," she smiled.

When Lucille heard my diagnosis, she took charge of my diet, and seeing to it I got the right supplements. She sold pharmaceuticals and could get what I needed practically free and in the latest forms.

It's up and running.

OK, so I did all the work, the money should be rolling in anytime now. Three weeks went by and I didn't get one nibble. It occurred to me that I had to promote the web site. I went through another round long days and nearly wiped out everything I had in reserve, but the business finally began to get customers. It didn't pay its way, but I was able to defray the cost. The good thing was that the hours necessary to keep it running was considerably less then the hours needed to get it going, which allowed me to work enough overtime to pay for the lack of income and keep us from going broke. I tracked the business and it showed a steady climb. Not fast, but steady. I figured if I could hold on for three years, I could reach break even. And hold on I did then for another year, I poured all the profit right back in and promoted the site, added to the line and changed the look just a little and made it attractive to plus sized women as well as cross-dressers.

Then at the end for the fourth year, the business took off like gangbusters. Two straight quarters of profit. By the third quarter, it brought in more than I made at the old 9-5. It was then that at the end of the year, it had made enough pay back all that I had invested, except my time. It was taking three to four hours a night to process all the orders.

The business is as simple in operation as it was difficult in setting up. I have suppliers that will drop-ship to my customers. They order, I forward orders to the appropriate supplier and pocket the difference. No inventory I sell for other people. Well, with the business showing a solid profit, I was ready to quit the 9-5, so I went to Lucille. I showed her the books from day one. She was a bit upset at first that I would risk the amount of money that went into the start-up but in the end, she was OK with it. But she wanted me to wait another year to quit. So for a year, I did double duty.

Oh, by the way, like most cross-dressers I made the mistake of not telling my wife about my little hobby. You know, I actually thought it would go away when I was married. I mean why would I need it? It was mostly a sex thing right? No, I found out it was much more then that. But I digress. In the fifth year of my business, I finally quit my job and went full-time as a work from home entrepreneur. It was great. I achieved every cross-dressers dream. I worked dressed. Lucille and I would get up and we'd have breakfast. She'd head out for work, while I stayed home. Before doing the breakfast dishes, I'd become Lynn, my alter ego. I'd spend the morning processing my orders and the afternoon looking for ways to improve my service. About an hour before Lucille was due to come home, I'd shower and become Ron again. It was great.

I had a perfect existence, even if my marriage had its share of problems. Oh don't get me wrong, my wife was great and I loved her more then life itself. But the secrecy and long hours at the computer in the first years of our marriage didn't lend itself to relationship building. Combine that with the fact that after about five years, marriages leave that honeymoon stage and begin their settle in process. Well, since our relationship was still shallow, we had it a bit rocky. I think she began to resent my mistress... that is my computer. I spent more time with it then I did with her. We tried to concentrate on quality time. You know do really fun things when we both took time off. Well, let me tell you, quality is good, but without quantity, you never get a deeper relationship then high school kids. I tried to make it up by giving her things, you know all the things that women say they want. The one thing I didn't give her was me. That, I gave the business!

Then one day disaster struck. It was two in the afternoon and I had just finished processing the overnight orders and was fixing lunch. I had a smoothie going in the blender. When it was done, I poured it into the waiting glass. When I turned around, I froze. There was my wife staring at my white turtleneck and gray box pleated skirt. Our eyes locked.

Finally she asked, "Ron, why in God's name are you dressed like that?"

"Lucille, you're home early."

What followed was a painful explanation of my 'hobby'. I told her about what I found out via the Internet. She said now she understood why I wanted an Internet business selling women's plus size clothing. In the end, her reaction was less then I'd have hoped for. As a matter of fact, it seamed to put cold water on our already cooling relationship. We hardly spoke for the next month. I even gave up my dressing while I worked. I was afraid that anytime, she would announce that she couldn't stand being married to a pervert and demand a divorce.

You can imagine my surprise and trepidation when over breakfast one Saturday she asked, "What do you call yourself?"

"What? I don't know what you mean, I'm Ron, like I've always been."

"You can't be Ron when you work, not the way you dress."

"Oh, well, I've given that up."

"You shouldn't you know. I finally took your advice and started using my computer to get online and research your problem. I understand that you "trans-people" have a... ah, oh yeah, a femme name. What do you call yourself?"

"Oh, ah, Lynn."

"OK Lynn, I've thought about it. Since you say you can't help yourself and that you have to play dress up, I've decided that it's OK with me if you do, providing you do it by my rules."

I was relieved. This meant that she was going to at least try to live with it. I knew the drill from my online friends. "Don't ever let me see you, don't ever let the neighbors or my friends, etc. find out." All those things most wives demand. You've heard them all before. Well, imagine the look on my face when what she wanted was the farthest thing from that.

"The first thing," she said, "you should do is get rid of all you men's underwear and move your girl's clothes into your closet.

"Next, make an appointment with an electrologist and get rid of all that unsightly facial hair. Get rid of those few hairs around your nipples as well." I had never been what you would call hairy. "What's more, you can quit changing clothes before I come home. No sense dirtying two sets of clothes every day. If my husband has enough of a feminine side that he has to wear women's clothes, then I might just as well get used to it.

"This last month, it's driven me nuts imagining what you have on while I'm at work. So now, I expect you to get up and do the womanly thing. Make yourself pretty, get breakfast for the family and see me off to work."

Now, that was a real change. By Monday morning I didn't own any men's underwear. My closet was full of dresses, skirts and blouses. They were all freshly laundered and pressed. My chest of drawers contained lingerie and pantyhose, just like any woman's. As a mater of fact, except on rare occasion, I haven't worn men's clothes since, all with Lucille's permission, nay insistence. I was even wearing perfume.

I was in cross-dresser's heaven. Monday evening Lucille was very attentive and had me doing all sorts of girlish things. I did her nails and brushed her hair. Of course since I was dressed for the part, I did the dishes. In the morning she left a list of household chores she wanted me to do. It was a pretty demanding list and I really had to hump to get it done after I took care of my business. I didn't mind, really. It was as if I was the housewife and my wife was the breadwinner. She often admonished me to be sure I looked pretty for her when she came home. In addition to all the other things I did, getting dinner became my exclusive job.

Lucille made another of her upgrades in the combination of vitamins I took. It wasn't unusual. She often exchanged one pill for another. I didn't pay too much attention to it when two new pills showed up in my regimen. The only thing that was unusual was that they came in plain bottles. I was to take one of the big ones and one of the little ones morning and evening. When I asked her about them, she just told me that they were something new her company was making. She told me that while they had been fully approved by the FDA, they hadn't developed the packaging yet.

Things went along nicely for about a month. Lucille even bought me presents. Mostly it was clothes she thought would look good on me. She seemed to have a thing for short skirts and dresses. On my own, I've always considered knee length to be short. An increasing number of the things she bought me were mid-thigh or shorter. One dress had a very full skirt and built in petticoats that made it stand out. I accused her of mugging cocktail waitress and stealing her uniform. That idea was reinforced when she wanted me to wear it with fishnet stockings and four-inch heels. For me two-inch was comfortable and three-inch was high. When I complained, she laughed and told me, since I thought I was dressed for the part, I could just serve her drinks that evening.

She drank a lot that evening. As she did, she got more and more demanding. It got to the point she demanded that I curtsy to her each time served her. I didn't want to cause any problems, so I went along with her. That Friday she came home with a French maid's uniform. She told me that I had looked so cute bobbing and curtsying that she wanted to try me as a maid for the weekend. I was relegated to the spare bedroom where I ran my business from the computer. In the morning, I was expected to be up early, dressed in my uniform and get my 'mistress' breakfast. Much to my later regret, I acceded to her demands.

She kept me hopping all weekend. Any little thing she wanted, she rang a bell and I had to fetch and carry for her. She gave me a list of chores to do over the weekend. I hand washed her delicates; I did her ironing and mending. Of course I prepared her meals and served them to her in the dinning room. However, I was the maid and had to eat in the kitchen.

Thankfully, she did give me some time to myself in the evening and I managed to forward all of my orders so that they would be shipped on time.

Monday morning I was informed that I had to have my uniform laundered and pressed by Friday, because she wanted a maid for the weekend again. I was allowed back in 'our' bedroom again that week. But on Friday, she told me to be in uniform when she came home.

As soon as she got home it started again in earnest. It was obvious she had stopped off for a drink on the way home. It seemed that nothing I could do would please her. She reprimanded me several times. The roast I had prepared was dry. I apologized and pointed out that I had, had to keep it warm for over an hour. With that, she became infuriated that I would suggest that it was her fault. After that, things went down hill. It seems I had chosen an inferior wine, like she could tell with the snoot full she came home with. I was slow in serving. On and on went the complaints. I was practically in tears by the time she finished dinner. I was late (according to her) coming to refresh her after dinner drink. To top that off, it was poorly made. That was the last straw.

Claiming that I had been asking for it all evening, she pulled across her knees and spanked me. I struggled and kicked, but she had caught me off guard. Using her left hand to hold my right arm in a hammerlock, she tucked my skirts under my elbow and whacked me soundly across my panties until I just whimpered. Not even as a child had I been spanked so thoroughly. I couldn't look her in the eye after that. I was glad that I had taken care of all the orders for my business before she came home because I didn't dare venture beyond the kitchen the rest of the evening.

I was up extra early on Saturday to process the overnight orders. I then got her breakfast assuming my maid's duties. I resolved that if she wanted a maid, then I'd be the best maid in the world. I exaggerated the bobs and curtsies. I punctuated every sentence I spoke with 'Ma'am' and when given a direct order I curtsied and said, "Yes, mistress." I hurried to carry out every order. When not taking care of a specific task, I busied myself with the dusting and such. I even got out our meager supply real silver and polished it, all without being told. She ate it up and seemed genuinely pleased.

Sunday after lunch she went out for a while. I took advantaged of the time to work my business. Just as I finished I heard her come in. I quickly rushed to front door to see if she needed anything. To my horror, Betty, our next door neighbor was with her. Betty is a widow. Her husband died in and industrial accident several years ago. He was well insured and all of their major debt had been covered by term policies and his life insurance left her with a very comfortable annuity that would, in all likelihood, out last Betty.

The other thing about Betty is that she has always been overly friendly to me, personally. Whenever I saw her outside, she would come over and talk and flirt, sometimes quite openly. Even Lucille had noticed. Well, here she was, looking at me in my maid's uniform all made up. I guess that'll cool her jets. I'm sure that was Lucille's plan in bring her in, unannounced.

"Betty, I don't believe you've met my maid Lynn. Say hello to Miss Betty, Lynn."

I curtsied and bobbed my head. "Hello Miss Betty," I parroted, my cheeks on fire.

There was a twinkle in her eyes. She had realized immediately who I was and was enjoying the knowledge. "Hello Lynn," she grinned. "Lucille, I'm jealous. I've always considered myself well off, but I never felt I could afford a maid." She was still grinning at me.

"Well, she's only here on the weekends, but I take full advantage of her then."

"Lynn, prepare a lunch for Miss Betty and me. Serve it on the patio. Bring us some iced coffee."

"Yes, ma'am."

They went outside and made themselves comfortable on our patio furniture. I prepared the coffees and went out to the patio. Betty still had a glint in her eyes.

"How did you ever talk him into it?" she asked.

"Oh, I didn't have to talk him into anything. It was quite the other way around. It was quite a shock when I came home and found him all dressed up. It took me nearly a month for me to warm up to the idea. Of course now, I wish we had come to this arrangement years ago."

I went back to the kitchen and began to fix chef's salad we had planned for lunch. The patio was just outside the kitchen and the window was open. I could hear Lucille filling in Betty on what duties I had taken over since becoming her maid. Listening to that I was reminded that Lucille and I used to share household chores, but in the three months since my cross-dressing was revealed, I slowly, but surely, had taken on every chore. In the two months since I had become the weekend maid, Lucille had become 'mistress of the manor'.

I quietly closed the window so I wouldn't have to listen to the conversation. I had to blink back my tears. 'Mistress' wouldn't be pleased if I ruined my make-up. The last thing I wanted was to give her any reason to spank me in front of Betty. Yes, she had spanked after that first time. Not often and not as severely, but I had been spanked, and spanked more deliberately. Lucille seemed to enjoy that I found it best to just go along and pretend to be cowed. It was just easier.

I served lunch, refreshed their drinks, then cleared away the dishes, put them into the dishwasher and was bending over to close the door when it happened. I felt a hand groping my pantied butt. It wasn't the first time Lucille had reached under my skirt. Frankly I found it sexy. I just didn't think she'd do it with someone in the house. What am I saying, I never thought there'd be someone in the house. I knew better then to object. I closed the door and straightened up.