The Dominatrix Business

I mingled with people through the streets, attracting occasional lingering glances as I darted past all them. I kept my head down and tried not to make eye contact. I felt every one of them was judging me as some sort of deviant. I made it back to the lobby and again the attendant stared at me the whole way back to the elevator. I got back up to the apartment and knocked on the door.

Amelia let me in and brought me through to the lounge where the two women were now seated with a glass of wine each.

"So were you humiliated?" Amelia asked?

"Thoroughly Mistress. I felt so ashamed I couldn't even look up."

"Did anyone say anything to you?"

"No Mistress."

"Did anyone touch you?"

"No Mistress."

"Did anything bad happen?"

"No Mistress."

"Now go round again, but this time I want to see a wide smile on your face. I want your head held high and proud and you will greet as many people as you can with a friendly and inviting demeanor."

I set off again, past the bored lobby attendant. This time I waved at her and smiled. She smiled and waved back. On my jog I tried to catch the eye of as many people as possible and smiled at them. Most people didn't acknowledge me and just tried to get past and go about their business as if I wasn't there, uninterested in the weirdo in the pantyhose and lipstick. But a couple of people did respond. I said hi and they greeted me back as I jogged past. I made it back up to the apartment. I felt strangely liberated, like I'd achieved some kind of personal growth. I didn't feel as embarrassed any more, the edge had been take off it.

"Any problems?" inquired Amelia

"No Mistress"

"So you understand? You're not doing anything wrong. There's nothing illegal about being dressed unconventionally. No one has any right to interfere with you or call you out. The humiliation is just all in your mind."

"Yes Mistress." And I did understand. It had been a genuinely educational experience. It had desensitized me to my absurd outfit.

Amelia's phone beeped and she checked her messages. She looked unhappy. "Problem with him again. I'll be back in five." Amelia disappeared out of the room.

My Mistress stared piercingly at me for a moment, thinking deeply about something while she was drinking. She was half way through a bottle in just the time it had taken me to run round the block twice. She was drinking it like water.

"I've got a problem. It's very personal, but since you're under my total control, you'll never tell anyone so I can tell you all I want." I listened, not that I could do anything else, but I was interested.

"My husband is an investment banker you know. He makes a lot of money and keeps me in comfort. We used to have a great time, flying all round the world." She gestured around. "This is only one of my five homes, he is living at one of our other properties right now."

It came as a surprise to me that she was attached, given how she was fooling around with me without any care. I didn't see any pictures of her husband anywhere as people often have in their home. She seemed to have no pictures at all.

"Two years ago he dropped a bombshell." She paused for a moment, sipping at her wine, leaving me in dramatic suspense. "He told me he wanted to be a woman"

I wasn't expecting that. Now I understood her situation.

"I immediately thought I'd divorce him. He didn't give a moments consideration to what it would do to me. But then when I reflected on it, who would look after me? So I stayed with him." She looked frustrated and upset.

"He still looks superficially male and can still work as normal, but he's... progressing... physically along his silly self indulgence."

"He's got a pussy now. He didn't consult me, one day he'd just done it on a whim. If you have enough money, doctors can be found. He called me from a hospital and asked me to come get him and I dutifully cared for him through his recovery. So now I'm stuck with a dickless man." She took a sip of wine and looked despondent.

"I couldn't bare to sleep in the same bed with him after that, he has his own separate room in all of our homes now. He knows he can't please me sexually so he suggested as a concession that I can fool around all I like with other men. But not just that..." She leaned forwards as if telling me a great secret. "He was actually eager about it and said he'd enjoy helping me arrange it. He started looking through dating sites and suggesting men I might want to fuck. I'm sure he gets off on the idea, some kind of thrill out of the idea that he can no longer fuck me."

"I'm hot right?" she shouted, staring at me straight in the eyes.

"You're gorgeous Mistress," I said honestly. It wasn't because she compelled me to say that, but she didn't really hear me anyway. I was sorry for her. She was consumed in her own thoughts.

"I'm a tiger in bed. Why would he want to deliberately make himself unable to have sex with me?" She paused and thought some more.

"It's not just that he wants to change gender. It's a fetish for him. He told me he enjoyed walking round his office knowing that he has no balls. It's something about the humiliation of being in such a highly charged testosterone driven environment as finance and he's there with his vagina and pink panties. He likes that intense anxious feeling that he has this big secret they all don't know."

"He's had all his body hair laser removed and he takes hormones. He's been edging towards looking as female as he can possibly be, but still just about appearing male enough to pass as one. But now that's not enough for him."

"He's got this plan, this fantasy, where he wants to give up his high paying job and be some kind of subservient secretary and I think he's going to go through with it. I told him he could be a powerful professional woman in finance, but that's not what he wants."

"He wants to get big tits and strut around in heels and a skirt. He'll look like a laughing stock. He hopes his new boss will slap his ass or something like that. He wants to feel subjugation. Then he says he wants to tell everyone he's now just a silly secretary and that he loves his new role. He wants to get off on his degradation."

"I asked him what was the root of all this nonsense. He said it all started with reading a genre of erotic fiction. It was called 'sissy' I think. He said it was just so incredibly seductive that he felt entranced by it, hypnotized even, that reading just one story was enough to capture his mind forever. Then he just couldn't stop himself and read more and more and each new story brought him in deeper and made escape impossible. It's like for any man who ever reads it, just one story and he'd be forever held by it, looking for ways to emasculate himself. It draws him in and warps his mind, piece by piece, a little at a time in ways he can't even imagine."

"But it's too late now. What's done is done."

"Our lifestyle isn't exactly all paid for, it's mostly debt and he's going to be no use for money soon to make the payments on it all. A bimbo secretary isn't exactly going to be covering the mortgage on multi million dollar apartments and he'll never be taken seriously again. He's going to be both a joke and broke but he doesn't care what he's doing to me. I'm done with him." She stared into space, then her eyes suddenly flicked to look at me. "I am sorry, I have a dim view of men at the moment. I might be abusing you for a certain vicarious revenge on him."

I felt uneasy at her use of those words. "But my real interest in you is more financial, I need to find myself my own independent large income and fast, which is not easy. And that's where you're going to help me." I had absolutely no idea what I was going to do about that. I had no money and no way of getting any. What could I possibly do?

"I've turned to being a dominatrix. I'm solving my own money problems by building a network of devoted financial submissives paying me what they can as tributes to show their devotion. I'm going to create for myself a large nest egg and be an independent woman of my own means."

"You're no use as a financial sub though given that you're unemployed. So I think you're going to be my suck boy instead."

"What's a suck boy?" I asked worried. It didn't sound like anything I even wanted to know about never mind wanted to be.

"You'll find that out later," she smiled wickedly. "Be assured you are key to all my plans."

Amelia walked back in. "Bad news. He's given us an ultimatum, that's another one gone unless we do something. At this rate of attrition we're going backwards. We've got two days. "

"Do you think you can you have him ready by then?" asked Mistress to Amalia while gesturing at me. I wasn't sure what this conversation was about.

Amelia stared at me thoughtfully. "It will be a challenge but I will do my best for you darling."

"I know I can count on you. Thank you so much."

Mistress turned to look at me and announced "You're going to belong to Aunt Amelia for a little while. You'll follow her commands exactly as you would mind. "

"That's Mistress Amelia, if you please." She rolled her eyes in frustration. "Follow me now slave."

Amelia started to walk out and I followed behind as if attached by an invisible leash. We took the elevator to the parking lot and she took me to her Mercedes. She stood by the rear door and waited. I stood and watched. Impatiently she ordered "Well open it girl!"

I opened the door for her and she got in the back. I understood now my role was not passenger but chauffeur. I got in the driving seat and buckled in. "Good." Amelia handed me the key. "I will give you directions."

I drove her for only a couple of miles but it took some time through the heavy traffic. Amelia flicked through her phone and just looked up occasionally to tell me which way to go. We parked in another block of apartments and took the elevator up to her place.

Her apartment was lavish and large. It was stylishly decorated and there was nothing out of place. The lounge was large with floor to ceiling windows looking into the city. "Right, we haven't got long to get you up to scratch so no time like the present."

She didn't tell me what to do or invite me to sit down, so I just stood in the middle of her lounge in lieu of no other instructions. After five minutes she returned from behind me. "Turn around," she ordered. As I did I was shocked to see her wearing a black leather corset, but more surprising than that she was sporting a realistic, flesh toned strap-on dildo.

"Down on your knees in front of me girl." I got down. "Open your mouth now."

She pushed the rubber cock past my lips. "There's a good girl," she said. "Now show me how you would suck it."

I had no idea how to suck a dick. I'd barely ever had mine sucked. I awkwardly bobbed my head backwards and forwards on the shaft something like I had seen girls do in porn. "No!" she barked. "Close your lips tightly around the shaft to form an airtight seal. Then get an even rhythm going." I followed he instructions. "One, two, three, one, two, three," she shouted like a music teacher giving the beat I was to follow. "Now, faster, more enthusiasm."

She told me about the importance of variation as a man would get quickly bored with my sucking if I did one thing too long. She showed me some other techniques, how I was to tease him by licking around the tip. When my jaw was too tired, to rest myself by licking along the length of the shaft.

After twenty minutes I was exhausted and she gave me some respite. "A good start girl. I think I'm going to turn you into an expert cock sucker yet."

She sent me out to collect take-out food, then later in the evening I got another extended round of cock sucking practice and finally she took off the dildo and told me to suck it on my own as she disappeared.

After a while she called me to her. I was surprised to see her lying in her underwear on the bed. "Stand in front of the bed and strip naked." I took off all my provided clothes and tossed them in a heap. "And wipe off that ghastly lipstick." I went over to her mirror and took it off with a Kleenex from her dresser.

She stared at me pensively for the a moment. "I so very much want a good hard fucking right now. I haven't had one in months." She thought for a moment more. "But I promised your Mistress I would keep you in a girly frame of mind. So climb over here and lick me out like a good lesbian."

She pulled off her panties and opened her legs to me. I put my head between her thighs and started licking. This was more familiar territory for me. She seemed to be enjoying it but pushed my head away after only a few minutes. I wasn't sure if I'd got her off or not, she didn't say. She told me to cuddle her.

I wrapped her in my arms and held her for maybe half an hour in silence. "You are such a good boy," she eventually said. It seems I was gender was fluid. She breathed out sharply with frustration.

"Damn it to hell", she suddenly declared. "I'll make you a girl tomorrow. Get hard and fuck me boy!"

My cock didn't need much encouragement and I was up in a moment. I climbed on her and penetrated her missionary style.

"Keep going, but don't you dare orgasm." I stayed hard but I couldn't approach a climax as I thrust in and out of her. After five minutes she tensed up and bit her lip and then relaxed. Perhaps I had achieved my assigned goal but I continued to fuck her regardless.

"That'll do nicely, stop now boy. Cuddle me again."

She rolled onto her side and I embraced her again, but she moved my hand down over her pussy. "Finger me." I massaged her clit for a while and finally she told me to stop, kissed me passionately and wanted her breasts sucking. Despite being denied an orgasm, I didn't mind having sex with her. She was much older than me, but I saw her beauty. She was in need of me, she was vulnerable in this moment, despite her emotionally prickly shell. It didn't matter that I was under her control, I would have made love to her anyway.

"Tell your Mistress nothing of this," she ordered. I wasn't sure how conflicting orders from the both of them might work out but I'd try to honor her request. It wasn't that late but she rolled over and went to sleep. I stayed with her until morning.

...

The next day Amelia was up bright an early. She was dressed in her professional business outfit with make-up done, ever impeccable and elegantly dressed. She required me to make her breakfast and then told me to get in the shower and shave off all my body hair - all of it. I should have nothing at all below my eyebrows. I shaved my legs, armpits, beard hair and all my pubic hair. It took me well over an hour but eventually I was completely smooth.

Then she mentioned I was to be "documented". I had no idea what this meant. She said would have to wait a little while as I had some redness from the skin irritation after shaving. She had me moisturize all over to help with that.

We instead moved onto walking in heels practice. She gave me a pair of hot pink scarpin shoes with a four or five inch stiletto heel. I just about squeezed into them. Then she put me in front of the TV with a video on how to walk sexily in such heels and told me to learn from it. The woman featured in the tutorial was walking like a fashion model, placing each foot in the same spot in front of her as she walked. She talked about looking directly ahead and letting your body follow you and walking heel to toe. I started walking up and down in the lounge on the hardwood floor, naked except for the heels. I was a little unsteady at first but quickly took to it with relative ease. Amelia did some work on her laptop. After twenty minutes my ankles ached and I called for her hoping for some rest. She told me not to interrupt her and walk until I was told me stop. I paid attention to the video again and tried to diligently copy the woman as best I could.

A while later and Amelia joined me, giving me some tips and watched me walk again and again, correcting my posture and correcting the sway of my hips. She went back to work, occasionally glancing up to observe my progress. I occasionally saw the screen of her laptop when I glanced in her direction. I was expecting spreadsheets and emails but I saw she was actually chatting to several people.

Eventually she told me I was "adequate" and told me to slip out of the shoes. I was delighted to be out of them as my feet and ankles were aching so much. Then I found out what being documented meant.

She noticed my dick was of, shall we say, normal size after last night and she struggled to find the right things to say, eventually asking me to recall the technique Mistress had used to shrink me down. I was back to having a nub again and Amelia seemed relieved. Presumably Mistress would not be happy if I was not seen anything but tiny. Perhaps it would give away the fact Amelia had fucked me, evidently without authorization.

She took down a painting in her apartment to leave a bare wall and pushed me up against it, then she photographed me naked. She told me to stand with my hands by my sides and smile. Then she took a close-up of my tiny penis. I grew anxious about what she was going to do with these pictures, but could do nothing to stop her.

She put lipstick on me and told me to put my finger in my mouth and close my eyes and photographed me in that pose. She had me touch my lip and look upwards like a ditsy airhead. Then she had me get down on my knees and gave me her realistic dildo with the strap-on attachment. She told me to put it in my mouth and look up at the camera and she took a close-up of my face. She laughed and showed me the picture. She had cropped out the harness and it looked just like I was sucking a real dick.

Next she had me get progressively more dressed. She put me in stockings and a garter belt with the heels, but no panties leaving my tiny penis and shaved pubic region framed by the garter. Then she added a matching bra and took more. She filled out my bra a little with some napkins. Then she put me in a short pink minidress and took a final set. She had me lift up my dress and expose my cock while biting my lip and looking ashamed.

She had me get out of the dress and give it back to her, which she hung up carefully. Next she transferred the pictures to her laptop, sat me down and scrolled through them, showing me each and every one and how ridiculous I looked.

"So you understand I have these?" she warned.

"Yes Mistress," I replied with some trepidation.

She copied them into an email. "And you understand how easily these can be sent?"

"Yes Mistress." I was terrified where they were going to go. She typed an email address starting with the name "my.findom" "and clicked send. I reasoned, I hoped, that was just my Mistress. I was somewhat relieved when my Mistress called Amelia a few moments later. She was on the phone for a couple of minutes, it seems she was pleased.

I got given more cock sucking practice, always more cock sucking practice, it was never ending. I was bored of it if anything. I could suck like a pro. Then we had lunch together.

"What's going to happen to me Mistress Amelia?" I took the opportunity to ask.

"You'll find out all about it tomorrow." She wouldn't be drawn and changed the subject. "You know I enjoyed last night."

"I did too Mistress," I said honestly. I really had liked having sex with her but I was her prisoner of a form and felt somewhat threatened by her. Maybe this was Stockholm syndrome.

"I'm an old divorcee and, well, having a young man like you available is a gift."

"You could find someone to love you, you're very attractive, you know."

"The problem with you is I don't know if you're just compelled to tell me what I want to hear." She thought for a moment "How old do you think I am?"