Transvestite Humiliation (M/t)

I wrote this almost twenty years ago. I have never reread it. I was exploring some of my feeling about crossdressers. I am the Dom.

Alex / Alexis – My Lovable Humiliation Slut

Alex and I had a date that night so I wasn’t surprised when he let himself in with his key.

At 5’8″ and 125 lbs. he’d never be called manly. Very very pale rather blank blue eyes and a weak chin made him look like the kind of guy who’d been picked on as a kid. Which he was. Treated nastily by his father as well.

Which is probably why he needed what I was able to give him. Anyone who meets me sees someone invincibly self-assured. I sometimes tell people that I could sell my surplus self-esteem but foreign dictators. It is a bit of a front but sometimes advertising is everything. I could also give him unconditional affection and complete fidelity. While I think of monogamy as pretty silly I’ve always been so. And I could give him the experiences you, gentle reader, will get a sample of as this narrative continues.

Alex gave me the most cursory brush against my lips and headed straight for the bathroom. Right now his mind was focused on remaking himself. Anybody who meets him can tell he’s a “nancy boy,” “jane girl,” that is, a femme gay male. What you can’t tell on sight is that he’s a transvestite. Dressing as a woman is his supreme pleasure in life. Probably more than I am, I’m not stupid enough to ask.

I grabbed a kitchen chair and parked myself outside the bathroom where I could watch. This was ‘his’ bathroom. It was my house but we did not live together. I had a second, smaller bathroom downstairs leaving this one a place he could keep a bewildering array of makeup pencils, creams, brushes and ointments.

He was nude except for hosiery and heels that he’d stepped into as soon as he could discard his office clothes. It slowed him down but he knew how much I enjoyed watching how the heels made his ass checks move while he was working on his face.

I can’t give you an intelligible description of what he did to his face. To me it just looked like he put stuff on, then wiped it off. Drew invisibly on his face with some sort of pencil. Even though his art only baffled me it was always very sexy to watch him work.

It took him about twenty minutes. When he was done his eyes had somehow become bright, beautiful and very womanly. His chin mysteriously looked much stronger. And in my mind was becoming a girl. A girl named Alexis.

Putting on a simple short black skirt and top took moments. She did struggle briefly to get his wig on. The hair wasn’t very long and was thick, black and straight. It had cost her more than I cared to think.

Finished she turned around for my approval. I always felt a glow of pride that my pretty guy was also a handsome woman. Since we were going out I could look but not touch.

Ready to leave he slung a handbag over her shoulder. Casual is very polite description of how I dress so I’m always ready. We got in her car for the very good reason that I don’t know how to drive (a long story of no interest here). I always call her my ‘chaufferette’ when we drive anywhere.

The restaurant was middling. I don’t care much about eating out. But Alexis does and I couldn’t think of a better way to spend the time to make her happy. Besides we weren’t really here to eat.

After we were seated out waiter asked the inevitable would we like anything to drink.

I ordered a scotch and soda. Alexis said she wanted a glass of wine. This was my cue.

“You silly bitch, I told you that I wouldn’t allow you any alcohol. How dare you defy me.”

She crimsoned instantly. “I’m sorry, please, I’m sorry.” Turning to the waiter, “I’ll have a coke.”

“The bitch will have a diet coke.” She softly whimpered agreement.

The waiter who’d been focusing on an empty point in the middle of the air quickly withdrew.

Alexis’s expression was unreadable: maybe kind of drunken, or something animal. Doubtlessly really humiliated the humiliation satisfied a deep hunger.

In a way the meal was already over before we’d eaten anything. We agreed we couldn’t take this too far. Someone might try to rescue the ‘little lady.’

So we quickly ate a bit of the food and left. The waiter was rewarded with a very generous tip.

Still flush with excitement from scene in the restaurant the kiss she gave me before we got in the car assured me I’d have a hot and passionate slut when we got home.

[ ]

The next afternoon Alexis and I were each in our own chair reading.

Her hair was of a cut that looked good on men or women and she didn’t have a wig on. At my request she was wearing her PVC thigh boots, hot pants and a tank top. She looked like a new wave hooker on her day off. I’d asked her to dress that way. She thought I just wanted her looking slutty. That was true enough but I had a special surprise for her.

“Make me a pot of coffee, sweet one.” She readily obliged feeling that minor domestic tasks made her more feminine.

She brought a cup in and sat it down beside me.

I raised my head and gave her what I hoped was a poisonously cold look. “What the fuck is this?”

“C-coffee.” I’d caught her off guard. She couldn’t imagine anything could be wrong.

“You are such a stupid slut. I told you to bring me a coke.”

“But- “

“Are you arguing with me, bitch-boy?” Mixing gender in my insults is always a warning she understands. There’s the hidden threat that I can wipe off the make up and take off the women’s clothing. That I can force Alexis to be Alex.

“No, no, please don’t be mad.” Absolutely meek and by now realizing something was about to happen.

“Get down on your hands and knees in front of me. Now, bitch.” It had actually taken a lot of effort at first for me to call her nasty names but that only excited her alot. “And keep your mouth shut.”

“You know where your collar is, bring it over. In your mouth.”

The collar was near so that was quickly done. I put it on and locked it.

“I should never let you take this off. You need it to remind you of who and what you are. Climb over my lap.”

She did. She felt very good there. So frail, completely mine.

“I think you deserve about fifty licks for your impudence. What do you think you deserve?”

She had started to drift towards subspace. “Whatever my Master demands, Sir.”

“You said that too easily. I think you are getting to used to your spankings. Get off my lap, I have a special treat for you.”

“Crawl over and bring me your leash.”

I think she was a little worried that I was going to spank her with it. We set hand spanking as a limit. I’d sometimes threaten to use the leash as a belt. If she’d been able to think clearly she’d know that I’d never violate our contract.

“Come on, we’re going walk downstairs. You know the way, stay on your hands and knees and go ahead of me.”

Crawling down stairs looked very awkward but she made it without mishap.

“Now we’re going out the back door, stay down and crawl out.”

She looked up at me wide-eyed. Outside the house, like this, would I really make her.

“I didn’t give you permission to look at me pussy-boy. Do you want worse than you are about to get.”

Too cowed to ask or say anything she just put her head back down and crawled out the door as I held it open.

When we were out on the grass I stopped and gave her leash a gentle tug, her signal to sit up on her knees and look me in the face.

“You’ve started to forget that you are mine to do with as I want. You are my pet. To remind you I’m going to take you on a walk around the edge of the yard. We are going to walk along all four sides of the yard. If you are lucky nobody will she you. If you aren’t …” I just shrugged.

The chances were vanishingly small that either of the people living at the side or rear would come out and se anything. There were trees and bushes long two of the fences blocking off lots of view. But in the small residual chance that they might lay the thrill.

Alexis was appalled. “Please, please … ” was all she said and it was pathetic.

I was heartless. “I could just lock you up here on the back porch for the evening. You are going to do exactly what I tell you and do it now. Make me wait and I’ll make it worse.”

I pulled on the leash and she followed.

“Walk in front of me. Don’t go too fast or I’ll make you crawl this route twice.”

She went at a moderate pace and I enjoyed watching her buns move back and forth as she crawled.

It seemed to take much longer than it could’ve as we went along one fence, another, yet another and eventually were back at the back door.

I opened the door and led her inside.

I removed the leash and pulled her up. She was limp so I picked her up in my arms and carried her upstairs.

Sitting in a chair I held her in my lap. She murmured something, I hadn’t any idea what but it was probably thanks. She was still recovering from the huge mental orgasm that only a satisfied sub feels and understands.

I knew she’d be incredibly loving for the rest of the day.

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