[Author's note: a collection of my writings on cross-dressing and erotic humiliation are available on Amazon, under the title: "A Treatise on the Sissy." -- Baloardo Gratiano.]
I began to regularly service Mrs. M. with my mouth, kneeling. There was no question of me penetrating her.
"You'd just come right away. Little dicked guys like you always do. But I'm going to help you. I'm going to get you used to being with a woman, then you won't be so overexcited." So she let me go down on her, and after she was finished—she would usually wipe her cunt on my face when she was done—I was allowed to jerk off wearing a rubber while I looked at her pussy.
After a week of this, she had the idea that I should kiss her asshole when I jerked off wearing the rubber. She was on her back, with her legs up: that way I had my nose in her pussy, and could enjoy its wonderful smell, while my mouth was on her ass. She didn't want me "bothering" her cunt after she came, but she did like me softly kissing her asshole. It was an act of homage,
After a few times, she asked me to lick it, which I did with great excitement. Finally I was putting my tongue into her asshole, really rimming her, licking it deeply, penetrating it fully with my tongue. I could sometimes taste her shit a little. We both knew it but we never talked about it—at first.
Then she started to have me lick her asshole when she was on all fours. Having her face away from me, and having her reach back to pull my face into her ass was very degrading. She began making me beg her to be allowed to lick her ass. To tell her out loud that I was her ass licker. I had to tell her I loved tasting her shit. That I wanted to be her toilet. It was very, very exciting.
She told me she was training me to be a toilet slave. That I would learn to love her asshole even more than her cunt. Because that was where I belonged, and what I deserved.
I kept my face very closely shaven, shaving three times each morning, with the grain, across it, and finally against it, to be sure my face stayed very smooth all the time. My face belonged between her legs, and I had to always be ready to serve her.
One day she had a surprise for me: a rubber pussy, a latex fleshlight sculpted at one end so it had labia. She told me that she was going to train me not to cum prematurely by humping my "training pussy." After I serviced her with my mouth, I had to spread a towel on the carpeted floor, lubricate my training pussy with KY, and hump it, holding it in place under me. She treated me just like a pet. "Go get your pussy toy! Good boy! Now get it ready! Now hump your little pussy toy, hump it good! You love your little pussy toy, don't you? Good boy. Make your little mess in the pussy toy. A rubber training pussy doesn't care how small your little thing is. It's just right for you, just what your deserve, and it's all that you deserve. Good boy!"
Although the supposed intention of this training was to make me not such a premature ejaculator, I found it terribly exciting. The shame of having to hump my pussy toy naked on the floor in front of Mrs. M. fully clothed made me cum even faster.
It became a kind of wonderful punishment. If I was too assertive in conversation, she would say, "I think you need to make your little mess. Go get your training pussy like a good boy; you need to hump that maleness out of you." I always had to show her my "little stiffy" first, and she would always laugh at how small it was.
The ultimate effect of this training was to make me so ashamed of my tiny thing I couldn't even get hard for my pussy toy. I finally wept trying to get hard for it. Mrs. M. was very consoling.
"That's good, I finally broke you. You know you can't do what a male does, you're not really a male to me, you never were. When you accepted that you had to use the training pussy, you were admitting that your little thing was useless to anyone. Jerking off in a rubber is as close as you'll ever come to fucking. The pussy toy helped you fully transition to the rubber, which is all you get from now on. It's time we started training you to be the girl you should have been. Time for you to really earn your panties."
From then on I wore a skirt when I did the housework, and a bra with breast forms. When I didn't have to do work that had me on my knees, like scrubbing the bathroom, I wore panty hose and heels. I learned to put on makeup.
"We need to beat all that maleness out of you," said Mrs. M. She had a leather paddle she used on my ass. I would have to stand in front of a mirror and lift my skirt. She would yank my panties down, and tell me "hide your little mistake, no one needs to see that." I covered my little thing and bent over so she could paddle me. She instructed me to look at myself in the mirror. "That's what a hole looks like when she's being punished. You need to understand you are now a submissive girl being paddled by the superior female who owns her. Say thank you at every stroke. Good girl!"
Mrs. M. bought a Stand To Pee device, a quite realistic latex penis through which she could urinate standing up. She trained me to kneel and accept her piss—to swallow it. I was now always tucked, and usually wore a panty girdle over my panties to be sure I had a nice flat front. It was a lot less trouble than taping, and had the advantage of guaranteeing that I couldn't play with myself. Male chastity devices are all easy to slip out of, but to pull down your jeans and peel down a panty girdle—that's a lot of work. It was bad enough I had to go through it all to piss.
So there I would be, kneeling, neutered by my panty girdle, drinking Mrs. M's piss "like a good girl."
"This is the only cock in this house. See to it you remember that, toilet girl."
My boy name, Damian, didn't make a lot of sense now, so she called me Diana; more usually "Toilet Slave Diana." And that's what I was. A dominant woman's housemaid and toilet slave. I drank her piss whenever she wished, and licked her ass several times a day. Either to show my gratitude, after a paddling, or after she had used the bathroom, as her bidet. She was always very clean, and there was no question of me literally serving as a toilet, but I did lick her there, and the faint bitter taste I sometimes experienced was quite enough to make it clear what I was. She never kissed me on the lips now. Sometimes she made me kneel in the bathroom with my face in the bowl for half an hour, looking into the white porcelain I was so used to scrubbing, to learn "by heart" that I was her toilet slave.
I felt my status as a dominant woman's toilet most poignantly when I pissed (sitting down of course.) After she had used me, my own piss smelled like hers, not like mine. I knew then I had become a real toilet.