A Sissy Success

What if you could leave behind who you are and become someone new? What if you could live a fantasy for a while? This is the service I offered. My clients had always been people who who felt overshadowed, who faded into the background like they didn't exist. People who's lives had become a series of routines, each day blurring into the next like an endless loop, but beneath an unassuming exterior lay unexplored secret desires. All they needed was a little push.

I helped sissies develop a new identity. They flew across the country to a new place where nobody knew them and just began again as a new person. It didn't have to be forever, they could go back to their old life if they wanted to and no one would be any the wiser. They'd just stay as long as they needed to.

My name is Madison. I'm a transsexual but my clients are not entirely the same as me. I feel comfortable and natural as a woman, this gender feels right for me, but for my clients it feels quite different. I enjoy the company of men and was never attracted to women, but the aspiring sissies who visit are usually straight as an arrow male heterosexuals. In reality they love women but they want to live out life as a heterosexual girl as a kind of game. Perhaps partially for the experience of something new, but I think a kind of humiliation kink has something to do with it. A little humiliation is what I try to deliver. Well actually, a lot of humiliation.

I enjoy humiliating my clients and they enjoy receiving it. The trick is finding the right level, which is different for each person and goes unspoken. They don't know themselves exactly where it is until they try it. I strive to go far enough to make them deeply uncomfortable, but not so far that they are too unhappy. I have to be a good judge of their type and empathetic to their needs. I'm partially a dominatrix, but I don't walk around wearing leather or carry a whip. I'm also a mentor and a friend. I arrange what my clients need. I am at their service, but they pretend to be at mine.

I've come to understand my customers crave a thrill that is something like being on a rollercoaster. They want the anticipation anxiety of being locked into an experience, such as when the rollercoaster is slowly climbing to the first precipice. At this point they want to get off the ride and are terrified of what they have got themselves into, but they just can't, they have chosen their path and the result is now inevitable. Then they want the horror of being being able to see the first steep drop, but they are forced to push through it no matter what. Then finally they want the rush as they fly down the slope, completely out of control.

It's a complicated mixture of feelings, they also want a little love and attention of the kind that I like too. They want some relief from their perhaps traditional male world. They want to enjoy the feeling of being admired and taken care of.

I help several clients at once, but today I was driving my latest customer, Jackson, from the airport. He was quiet and unsure of himself, as many sissies are. He was a little younger than most of my clients, aged 25, quite slight with blonde hair. I remember thinking he was going to turn out to be a cutie.

I drove him to a small house in the suburbs that he had taken out a year's lease on, he'd paid up front in full. My clients are usually moderately wealthy, they have to be to afford to start a new life like this and pay my fee. Jackson is something to do with finance but I don't understand quite what. Bankers though are quite useful to know, in fact one gave me an idea to help with the experience I offered.

My clients arrive with no luggage, only the shirt on their backs. They are not poor, but they may as well be. A previous customer had suggest a method of enhancing the feeling of being locked into the sissy experience, which is what they all want to feel. He suggested putting all his money into a bond that cannot be accessed for some period of time. This is what I have had Jackson do. He had locked away all his money so that not even he can touch it for 12 months no matter how much he wants to. For the next year he has not a cent to his name and is completely dependent on me. He had given me access to some funds that I would spend or drip feed back to him at my discretion, dependent on his good behavior.

We arrived at his unassuming single family home on a nondescript dead end. It was two bedrooms with a single garage. I'd picked up the keys from the Realtor and had dealt with turning on the internet and utilities. I had asked Jackson to inform them I was his cousin and was helping him get settled.

I got him to help me carry some things from the trunk into the house and place it all in the lounge. I had a couple of bags and a metal trash can. The house was minimally furnished with the bare essentials and neutral painted walls. "Oh we'll make the place nice." I told him.

I closed the curtains in the lounge for a little privacy. "Now, you strip for me honey." He was uncertain at being given an unusual instruction so suddenly and forthrightly. "Take all of your clothes off honey. Everything." He slowly did as he was instructed, unsure if he was doing the right thing or somehow making an ass of himself, and stood there naked. I took his pants and searched the pockets, finding his wallet. Even though he was told to arrive with nothing, I was pretty certain he wouldn't. He couldn't be sure I'd really meet him at the airport or maybe this was all some kind of joke. He'd have to leave himself the means to get home if it all went wrong. That only made sense.

"Bad boy! Now, you won't be needing this." I waved it at him disapprovingly. I looked inside and found a little over a hundred dollars. I stole it and tucked the cash down my cleavage into my bra whilst looking him in the eyes sternly. He didn't react, he knew I was in control. There was a driving license, which I kept too and a single credit card. Now if I had just kept the card, he might order another one. I searched the other pockets and found his phone. I made him call the bank and cancel the card while I watched then I tossed it into the trash can together with the now empty wallet. I took his phone and made him give me the unlock code. He'd be getting the phone back, but with a few small adjustments.

From the bags I pulled out some lotions and shaving things and told him to go to the bathroom and shave off all his body hair in the shower. That would keep him occupied for a while. In the meantime, picked up his mail and opened it. Conveniently something I was looking for was in the mailbox at the right time. Government works slowly and this was something we'd started months ago. I'd made sure it was on the way before I told him to fly over.

Jackson came out of the shower as I was working on his phone. I inspected him thoroughly and pointed out areas he missed and told him to go over it again and get a closer shave. He'd completely missed out his crotch and armpits and I had to explain to him what I meant by "everywhere". I wanted to see no hair below the eyebrows. He'd soon receive a real waxing but I just needed to quickly get him up to the minimum standard. When he was finally done, I made sure he was covered in lotion and explained to him a skin care regime.

I had him put his clothes in the wastebasket and took him out into the yard with the metal can. I took a quick peek to make sure we were in a spot that was not overlooked by the neighbors. Then I handed him some lighter fuel and told him to set fire to it all. I could have just thrown his clothes in the trash, but it was a form of ceremony to mark the end of his male life. "You're mine now," I told him.

The flames died down quickly and I took him back to the lounge and pulled out some new clothes for him. I had a white bodysuit and a short, tight, pink miniskirt with a bra and panties. I told him to put them on. He'd never dealt with a bodysuit before and I had to help him although he seemed to be an expert with the bra. Next I had him sit down and did his makeup. I got his beard to cover with a heavy foundation popular with cross-dressers and put on a little light lipstick, eyeliner, eyeshadow and did his eyebrows. He looked much better now and was starting to transform

I pulled back his blonde hair, styled it a little. He didn't really have enough hair for a female style but that would have to do. Next I put him in a pair of pink sandal heels. "Stand up," I instructed. I opened the curtains and he glanced out, anxious to see if there was anyone outdoors who might see him. He wouldn't completely pass inspection as a woman, but he wasn't too obvious at a glance. You could still tell his male features and he was a little tall, maybe 6 foot 1 in the heels but not excessively tall.

"Now walk up and down a little," I instructed. He wobbled on the heels, but with a small amount of instruction got the idea of it.

"Don't you look sweet." I pouted at him. He looked embarrassed. "So rule number one for you is you are forbidden to ever wear pants. I know women wear pants, but you don't. You will only wear skirts above the knee. Clear?" He nodded.

"Good girl, you're going to be a she from now on." I smiled. I think she wasn't sure what she got herself into but I was about to amp it up. I handed her a letter from the mail I opened and told her to read it. She'd given me her signature some months ago to use as I needed, but I hadn't showed her what she had signed. It was a legal petition to change her name.

"You're now Aurora honey," I squealed with delight and clapped my hands together. I liked that name. It was a reasonably common female name and perfectly decent. As much I would have liked, I couldn't call her something obscene or sexual on a real legal document, but Aurora was just a little exotic, like the name a stripper might choose for her performance persona. I just wanted to set her apart. "In law you're a woman too, your gender, at least in this state, is now female." She looked worried.

"But what happens, after? You know, when we're done?" she asked with a look of panic.

"You just change it back. I checked you could," I reassured her but she was still uneasy. "You can look it all up, don't worry, there's no problem."

I gave her a little time to settle until she was comfortable again, then it was time to make progress. "Now, let's go meet the neighbors." Her face dropped. I grabbed her by the hand and dragged her outdoors into the bright sun. Her head darted around looking for anyone who might be watching. There was a middle-aged man across the street washing his car. I smiled and strode towards him pulling my unwilling client behind me. "Hello!" I vivaciously greeted him with a wave. "This is Aurora, your new neighbor," I introduced her. "She's my cousin. Don't mind her, she's just a little shy. She's new to the area."

"Oh hey there, I'm Jordan," he said extending his hand warmly. He didn't seem fazed by us at all, he was the right person to start with. I shook it and beckoned Aurora to do the same. She meekly did so and looked down at the ground the whole time. I filled in a little small talk and then he clearly wanted to get on with his work. "Well, nice to meet you both, I just told my wife I'd clean this then I have to get to the store." I told him it was great to see him and he should come over. Then we moved onto a different neighbor.

"Aurora, smile!" I instructed her. "Lift your head." An elderly woman answered the door at one house. She was polite but seemed wary and suspicious of us. I hoped she was the local tattle-tale, who would tell everyone there one of those women who looked like a man staying down the street.

Aurora's immediate next door neighbor was great, a middle aged Italian sounding woman called Lucia. She invited us in, I dragged the reluctant Aurora inside. We were invited to sit at her dining table. Lucia offered us wine and food. I suggested a large glass for Aurora to loosen her up. We talked for half an hour and she told us all about her work. I told her Aurora was new to the area, she was looking for a job and also a boyfriend. Lucia seemed really interested in the subject of a boyfriend and started telling us about bars to go to. She gently probed Aurora about what kind of man she was looking for. Did she like them older or her own age? Aurora evaded the questions. It it was at this point I noticed she was looking especially uncomfortable and was flushing bright red. I looked down and she had a very obvious bulge developing at the front of her tight skirt.

I decided we had talked to the neighbors enough for now. I made an excuse, apologized that we had forgotten some appointment and what an air-head I was and quickly left. Fortunately, I had automatically picked up my bag. I passed it to Aurora to cover her embarrassment until we were out of the house. I took her back inside her own place and she had a wet patch at the front. I knew now that the idea of a boyfriend was a major trigger for her.

"Well, looks like it's laundry day for you." I said looking down at the wet spot. "When you go grocery shopping, you'll need to buy some sanitary pads to catch these little accidents in the future. That's another rule, you must wear a sanitary pad at all times." She nodded.

I think I had pushed her far enough for one day and she was probably tired from traveling. "Now, I'm going to leave you now. I want you to clean up and wash your clothes. I'll order you a few groceries to get you through the evening and I'll be back tomorrow morning."

I picked up her phone and handed it back to her. "I've made a few alterations. There's now an app installed that lets me know your location. Don't try and disable it or I'll be very unhappy. I want you to carry this phone with you at all times. I've also installed an allowance app."

The allowance app was meant for college students such that they could receive money from their parents. You could pay at stores with the phone. Controlling her spending was a way of keeping her in order and could be used as a punishment for bad behavior. It was her own money I would be sending her but I was in complete control. I could take the money back at any time and set her balance to zero.

"If you're a good girl, you'll receive a small amount each day to cover food and small expenses. If you want to buy something bigger you'll have to ask my permission. Now I think you have been good today, so there's $20 on your account."

"Oh I also changed your background. Take a look." She opened the phone and the background was set to a handsome male celebrity. "I've set a password so only I can change it. Also I have an app to monitor everything you do on the phone."

"One more thing," I tossed her a bag of electrical items. "There's a bunch of cameras here. I want you to get them set up with one in every room. It'll give you something to figure out this evening."

I left her alone for the evening, I saw she didn't leave the house. Or at least her phone didn't. I arrived early the next morning and rang the bell.

She answered the door with her head poking around. When I came in she was naked. She looked a mess. I told her to get ready and she changed into the same clothes as the previous day, the only clothes she had. While she was doing that I checked out the cameras I asked her to install, which were all in place. When she came out I showed her a video feed on my phone. I showed her how I could view any of the cameras at any time. "No more privacy for you, at least from me. I see all."

I did her make-up and fixed her hair again and then took her out to the car. I drove Aurora to a small store in the city that specializes in outfits for cross-dressers. I was friendly with the owner and brought her a lot of business. "Madison darling," the exuberant drag queen owner greeted me.

"Hey Grace, here's my latest project. This is Aurora. See if you can work your magic."

"Delighted darling, oh she's lovely."

I discussed with Grace what we were going for. Aurora didn't get a lot of choice in the matter and I left her there for most of the day. When I came back Aurora was wearing a tight red red dress with stockings and matching heels. She now had a wig with long blonde curls. She had little budding breasts and a slightly more feminine figure. She must be wearing a foundation garment.

"Oh excellent work, you work wonders as ever," I complimented enthusiastically. I walked around and examined her.

"She's tucked. I wasn't sure if you wanted flat and feminine or a little surprise?"

I thought for a moment. If the client looked quite masculine, as many did, I often had them tucked but wearing a prosthetic giving them a prominent camel toe. He's humiliated by the implication of having no penis even though he is obviously a man. Aurora looked somewhat passably feminine and people might not notice, I thought particularly after the display yesterday, she might be more embarrassed by her little bulge in a tight outfit.

"Bulge I think, we'll go a little more femboy. Can we also have slightly bigger breasts?"

"Sure thing." Grace pulled out some inserts and replaced them with bigger ones."

"Oh, Aurora, tell Madison ..."

"I can do my own make-up now. Do you like it?" she asked enthusiastically.

Her look was simple but acceptable.

"She truly did it all on her own. She's been practicing all day."

"I'm very proud of you honey," I complimented her. "You look fabulous." She seemed to blush and be pleased.

"Well, I think we have to go." It was nearly 8pm. Grace had stayed open late until the job was done as a favor to me and I settled with her with a big tip from Aurora's money. We loaded up the car with a few outfits of Grace's choice, some cross-dressing specific items and shoes.

I took her to a gay friendly bar not far away. She wasn't the only cross-dresser in there. She didn't seem concerned. I wonder with her full day of cross-dressing if she was getting too comfortable. Well if that was the case, I had plans to switch it up.

"I'm going to leave you now for a while," I said. Aurora looked concerned. "Don't worry, you can just sit here on your own and play with your phone. Take a few selfies."

I walked out and nodded at a man sat by the bar. I didn't drive off, I just went and sat in my car, waiting for a call I thought would probably be coming. About 20 minutes later I got a message. I walked back inside and my male accomplice was sat with Aurora. Her body language was looking uncomfortable. Her legs and feet were pointed away from him.

I sat down with them and turned to Aurora. "Oh I see you met Xavier." I turned to him and asked "Is she a little reluctant?"

"I asked her to come home with me, but she doesn't want to."

"Xavier is a good friend of mine. There's a new rule for you now. Any time a man makes an advance, you have to agree. Understand?"

She didn't acknowledge and looked firmly down and away from me. "It's still early but I think you should go with Xavier now." I looked at him and smiled. "I'll pick you up at midnight."

About an hour later I got a photo from Xavier with Aurora naked aside from her wig and on her knees, a glum expression on her face. I wondered if they were possibly getting along, however Xavier called me about 10pm and said all was not well.

I drove to his place and Aurora was naked on his sofa but still looking unhappy.

"So what happened?"

"Well she licked it once, but that's as far as we got."

"Well it's a start. Come on girl, down on your knees for your man."

"I can't do it, I'm sorry. I want to go home." She was being petulant.

I looked at her with a stern expression like a chastising parent. "Just try it, just a little." I got down on my knees and motioned her to join me, pointing at the ground beside me. She eventually complied and got down beside me, very slowly and deliberately with clear unwillingness.