Married for Money

This is a darker story with the main character undergoing forced feminization, reluctant sex, and considerable humiliation. As with most of mine, there is a brighter end, but only after a long period of darkness.

The person who marries for money will earn it.

************************************************

Okay, I married a woman for her money. I grew up not having a lot, though I was charming, well spoken, moderately smart and not bad looking. I met Cheryl and she seemed taken with me. When I found out she came from real money, I latched onto her so damned fast. Her parents insisted on a pre-nup, and I was so eager to get what I could that I signed with no hesitation.

I got a decent job because her money helped me get it. It paid decently, but of course it was her money that paid our bills. It was great at first -- the sex was decent, and I got clothes, cars, vacations, toys, and houses that I'd never have had a shot at otherwise. After a while, I grew resentful of the fact that she had all the money and controlled all the money in our marriage.

Okay, I had money from my job, which gave me a little bit to play with, just nothing close to what Cheryl and her family had. The money I had, along with my position and my charm gave me a chance to have affairs with a number of very beautiful women -- women far more beautiful than Cheryl. My ego was soothed by having these affairs.

So I should have known that eventually Cheryl would catch on, I just never imagined what the consequences of being caught might be. I'd been able to charm my way in and out of all manner of things over the years, I figured whatever happened, I'd be able to charm my way out of that too. Damn was I ever wrong.

I told the people at my office I was going to a business lunch and might be gone longer than an hour. I was actually going to see Kelli and fuck her silly for as long as I could. Kelli was the girl of the week for this week. Last week it had been Juli, and the week before that Patti. After a week, I tended to be tired of them, though I might give them another go a couple months later.

I had a great time and got off several times while I was with Kelli. I got back to my office a couple hours later to find Cheryl sitting at my desk. I was kind of surprised to see her and stopped in shock. She waved me toward one of the other chairs in my office.

"Have a seat, Phil."

"What's up, Cheryl?"

"Your free ride is what's up."

"What do you mean?"

"I'm tired of you riding on my family's money, while fucking everything female with no consequences."

"Come on, Cheryl, baby, that's not true."

"Of course it's true. I have documentation on more than a dozen different women that you've fucked, just in the last few months."

"I'm friendly and I socialize with women, but that doesn't mean..."

"So you mean to tell me that these aren't pictures of you fucking the slut you were with today?"

Cheryl spread out several pix of me with Kelli, some of which had my face very clearly, and some of which showed me fucking her. One pic had her sucking my cock with my face in clear view.

"Photoshop can make things appear to be true that really aren't."

"Those aren't photoshopped and you damned well know it. And photo expects can testify to that if need be."

"So I had an affair with that woman. I really am sorry, and I swear it won't happen again."

"I have similar pix, including video of you with a number of other women."

"You and I have gone through a bad spell lately, but..."

"Cut the bullshit, Phil. You've been doing this for a long damned time, and with a hell of a lot of women."

"Cheryl, I know you assume the worst, but it's not as bad as you're making it out to be."

"It's a shit load worse than I'm making it out to be."

I made every excuse I could, but to no avail. Cheryl had solid documentation, including legal depositions from a number of women that I'd fucked. It was totally my fault, and I'd been caught. Most of them I'd dropped cold after fucking them a few times and that left a trail of bitter women behind me. After I finally ran out of excuses, I tried to put it all off.

"Cheryl, I truly am sorry and will try to make it up to you, but I have to get back to work."

"No, Phil. You don't work here any longer."

"What do you mean?"

"My money got you this job, and my money is taking it away."

"Come on, baby. Don't do this."

"It's already done. You won't even get a job scrubbing toilets, much less anything that will pay decently."

"So I need to leave town?"

"My family has connections in every advanced country. Your reputation will follow you everywhere."

"Now you're bullshitting me."

Cheryl smiled, a very evil grin, and sat back at what had been my desk. "I don't make idle threats."

"So what do you want?"

"You will do what I say, when I say it, and without question."

"And if I don't?"

"I've already made sure your little girlfriends won't take you in, and none of your male friends will either."

"So I sleep on the streets?"

"Until you're arrested for vagrancy, then you can share a cell, with someone who'll make you his prison bitch."

"You can't possibly have everything tied up that solid."

"Phil, I have the money to make that happen. If you find something I missed, I'll get it covered fast."

"I do have resources, too."

"Phil, you've blown nearly every cent you have on alcohol, drugs, sex, and gambling."

"What about cars and..."

"Nearly every bit of that is in my name. What little you have won't last long."

"So what do you want?"

"You start by putting that on."

Cheryl waved at one corner of the office, where I saw what looked like a French maid outfit hanging. I got up and walked over there. There was a black dress that would come well above the knees, stockings and a garter belt, a white half apron, lacy panties, and high heels. I stood just looking at it for a minute, not really believing it.

"You've got to be kidding."

"Not one bit. Put it on."

"There's no way in hell I'm wearing that."

"You'll wear it or else."

I turned and walked briskly out of the office and kept going. I went to where I had parked my car, and it was gone. Cheryl was clearly a step ahead of me. I pulled out my phone and found I no longer had phone service. I went to a store nearby to get a burner phone, but I carry little cash and found all my credit cards were blocked.

One of my girlfriends lived not too far off, so I walked over there. I knocked on her door. When she opened it, she had the security chain on. She saw me and slammed the door before I could react. She spoke to me through the closed door.

"Leave, and don't come back. Forget you ever knew me."

"Come on, baby. Please."

"If you don't leave, I'm calling the police."

I tried for a couple of minutes to persuade her to open up, then decided to get the hell out of there just in case the police showed up. I no more than got out of the building before I saw two policemen go in the building I'd just left. I walked briskly down the block to get as far from the police as possible. As I neared the end of the block, I saw Cheryl standing by one of her cars. She waved toward the door to the back seat.

"Get it. Your new outfit is on the back seat."

"You're not really going to make me wear that?"

It was obvious that she intended to humiliate me, the only question being for how long. She clearly had planned this all out and without cash or a phone, I wasn't going to be able to figure a way around it. I decided to do what she wanted, hoping that she would tire of the game or that I would figure out something else less humiliating.

I got in the back seat and sure enough the maid outfit was there. Cheryl got in the car as well, and she had a driver who seemed to have a major smirk painted on his face. I sat there looking at the outfit, when Cheryl turned to me.

"Take off your clothes and put that on -- Now!"

"Here in the car?"

"I don't want any argument or any questions. I want you to do what you're told, when you're told."

I took off my suit coat, slowly, and put it to one side. I looked at Cheryl who looked impatient and gestured for me to continue. I took my necktie off and put it with my coat. I slowly unbuttoned my dress shirt, then pulled it out of my pants. I unbuttoned the cuffs on the shirt and took a deep breath before taking it off.

"I've seen the videos. It doesn't take you that long to get undressed when one of your sluts wants you to fuck her. Now speed it up or get out at the next light."

I was wearing an undershirt, so I pulled that off. My sparse chest hair stuck out as I sat there. I untied and took off both shoes and socks. All I had on still was pants and boxer shorts. I unbuckled my belt then open the button on my slacks and unzipped them. I kept hoping against hope that she would relent and tell me she was kidding, but no such luck. I pulled off my pants and sat there in my boxers.

"That comes off too. Now move it."

I took off my boxer shorts and sat there naked until she handed me the panties. I pulled them on so I'd have at least something covering me. I had to tuck my dick and balls back between my legs and the panties seemed to hide them away and look almost as though I had none. It wasn't especially comfortable, but luckily I was so humiliated I had no hard-on.

Cheryl handed me the dress and I slipped it over my head and pulled it down to cover as much as I could. She handed me stockings and as I was pulling them up my legs, Cheryl put a blonde wig on my head. She had me put on a garter belt, then fasten my stockings to the garter belt. She gave me some heels to put on, which fit decently. I was surprised that everything fit well, but Cheryl knew my clothing sizes.

I put on the half apron, and apart from the lack of a bust looked pretty much like a French maid. Shortly after, the driver pulled into a parking lot next to a large container. It was a donation box and Cheryl had him put all the clothes I'd taken off into that donation box. That bothered me, but I figured I had more regular clothes at the house and could change there.

We pulled up at the house and the driver let us out. Cheryl and I went in the front door and were met by Jacki and Marie, Cheryl's two maids. I had slept with both of them in the past and we were met with yet more smirks as they saw me. Cheryl pushed me toward the two of them. Personally I just wanted to run to my room and put on regular clothes, but Cheryl was clearly enjoying this.

"I have a new maid, Phyllis. Would you two get her cleaned up, please?"

"Phyllis?"

"Yes, that's your name now?"

"Haven't you had enough fun?"

"The fun is only beginning. Ladies, Phyllis has too much body hair. It all has to go. Phyllis, you will cooperate with them. If she doesn't feel free to punish her."

The two women took me by the hand and led me to the maid's quarters. There they stripped my clothing off then put depilatory over much of my body. They shaved my underarms and around my dick and balls. I kept wondering just how far they were going to take this -- how far Cheryl told them to take this.

At one point I got a little fed up with it all and tried pulling away from them. The two were surprisingly strong and got me across Marie's knee, where she proceeded to take a paddle and spank me hard. I couldn't believe that they could or would do that, but they did. I tried to get away, but they held me tight while Marie turned my bottom very red. I finally realized I wasn't going to get away, so I let them do what they wanted. They finished paddling me shortly after.

They had me put my panties back on that hid my boy parts. I sat there in nothing but panties with a very sore bottom, wondering how I was supposed to get away from all this. About that time, they put two things against my chest and told me to hold them or I'd be paddled even worse. They were breast forms that the women had put glue on and were gluing to my now hairless chest.

That was a pain. Even getting away from them and finding my regular clothes, I'd still have to figure out how to get those damned boobs off me. Once the glue was dry, they put a bra on me and I put the rest of my maid's outfit back on. I still had on the blonde wig and they proceeded to glue that on as well. Then they sat me down and put makeup on me.

"We're using long lasting makeup, so it won't come off as easily."

"Do we have to?"

"Madame's orders, and you're going to have to learn to do your own makeup so pay attention."

"This is ridiculous."

"Do what you're told or you'll be spanked again. And if necessary, we'll get the driver and he can really lay into you with the paddle."

It was late afternoon by the time they were done with me, and they told me we would all need to serve dinner for Cheryl and some guests that evening. I didn't want any of Cheryl's guests to see me like this, but they told me I'd damned well better do that. I looked in the mirror and could barely recognize myself, and hoped none of the guests would know me.

Now I've never been particularly large for a man, around 5'6" and 130 pounds, and my features have always been somewhat delicate. I did have an Adam's apple, but they put a choker on me that largely hid that. When I looked in the mirror, I looked about the same as the other two, particularly since they were both about my size.

Cheryl had five guests for dinner and the three of us quietly served the meal to the assembled group. It seemed like everything would go without notice until one of the guests made a remark.

"It looks like you have a new maid."

"Her name is Phyllis, but some of you used to know her as Phil."

I could tell I turned bright red and wanted to rush from the room. Jacki and Marie blocked my way and Cheryl spoke to me.

"Phyllis, come over here so everyone can get a good look at you."

I could hear snickers from some of the guests as I walked over for them to look at me more carefully. I know Cheryl wanted to humiliate me but this had gone well beyond what I'd even have expected of her. As I had leaned down serving food before, I know some of the men had good a look at my boobs, which looked quite real.

Cheryl had me turn around so everyone could see me front and back, then she had me lean over to show my boobs shifting so everyone could get a good look at them. When I thought it was all over, Cheryl lifted my skirt showing my panties to the assembled crowd. I was embarrassed beyond belief, but knew that even if I escaped to my room, I'd have to figure out what to do with the boobs, and how to get off the long lasting makeup.

"Pretty panties, and no trace of a bulge."

"It will still take some training before she is a proper maid, but this is a start."

Cheryl let go of my dress and I quickly scurried to the kitchen, hoping I could hide out there the rest of the evening. It was not to be. Jacki and Marie came back and said that Cheryl wanted me to serve dessert to the guests. I took a tray of desserts out and began to serve them. As I did, one of the men grabbed my ass. I tried pulling away, but to no avail.

"Phyllis, don't be rude to our guest. He's just showing his appreciation for your appearance."

I stood there as he played with my ass, then had to go around so each of the other men could do so as well.

"Damn, I wouldn't mind getting to know that better."

"Now Frank, they are maids, not hookers."

"Can't blame a man for trying, can you?"

As soon as the men were done pawing me, I escaped to the kitchen. Marie, Jacki, and the cook were eating and had a place set for me to have dinner with them. Normally I'd have been offended at having to eat in the kitchen with the help, but compared to what I'd already been through, it was pretty damned benign in comparison.

"Once we're done eating, we need to clean up the dining room and serve drinks in the study."

"I'll be happy to clean up the dining room." I wanted anything that would get me away from Cheryl's guests.

"Madame made it clear she wants you to serve drinks."

The six people were in the study and I went in to get them drinks while Marie and Jacki cleaned up the dining room and washed the dishes. The three women just wanted wine, which I got for them very quickly and easily. The three men wanted mixed drinks, but that was no problem. Cheryl had a fully stocked bar and I'd been a bartender in my youth before I met Cheryl.

Once I had drinks for everyone, I tried to retreat to the bar to wait on more drink orders, but some of the men wanted none of that. Frank wanted me to sit on his lap, and though I didn't want to, Cheryl made it clear that I should. Needless to say, Frank had his hands all over my ass and my boobs. He even tried running his hand up under my dress. I kept my legs tight together and as he reached my panties, someone asked for a drink.

I extricated myself from Frank and checked everyone's drinks getting fresh ones for all. I stayed as far away from Frank as I could and tried to stay busy with drinks all the time after that. Cheryl asked me to get another bottle of wine from the wine cellar, and I took my time doing that. By the time I got back, everyone needed fresh drinks again.

I dodged Frank especially as much as possible until the dinner party finally broke up and people left. As he was leaving, Frank ran his hand under my dress all the way up to my ass. Of course, I was the maid who had to help everyone get jackets, coats, and purses as they left. Finally, everyone was gone, and I was at the entrance with Cheryl.

"How much longer are you going to do this to me?"

"You've been running around on me literally for years. You think you can atone for that in one night?"

"So can I go to my room?"

"You have a room in the maid's quarters now."

"What about my bedroom?"

"It's now a guest bedroom."

"But my clothes there?"

"They were all donated to charity. Your maid's outfits, along with some casual skirts and dresses are in your new quarters."

"I don't get to dress like a man?"

"You're now Phyllis, the maid."

"And my pay as a maid?"

"You'll have food, housing, and clothing. Any extra pay will make a tiny dent in what I've spent on you in the past."

"So that's the way it is?"

"I know you're familiar with the servant's quarters, having gone there to fuck maids in the past. You have a room there, and I strongly advise you to keep your hands off the other maids now."

"And if I don't?"

"It's easy to turn a stallion into a gelding."

I went to my new room and the other two helped me take off my long term makeup. Most of it came off fine, though the lipstick and some of the other products they used left residual stain on my lips and elsewhere. They helped me out of my bra, and showed me a negligee that was apparently mine. I went to bed and slept poorly, trying vainly to think of any way out of this.

.................................................................................................................

When Cheryl was at the house, and especially when she had guests, we were quite busy taking care of all that. When Cheryl was out, we cleaned and did laundry, but it was far less onerous. I checked my old bedroom and sure enough all my clothes were gone from there. The driver was the only other male on premises and he was 6'2" and 200 pounds. His clothes would never fit me.

There of course were phones, and when I had free time, I called everyone I knew to see if anyone would help me. Many of them simply laughed at me. The nicer ones were apologetic as they turned me down. I even called my relatives, though I knew they were not well off. While they weren't well off, they weren't as bad off as they used to be.

"Cheryl helped us out, but made it very clear we weren't to help you."

"But I'm your blood."