We settled on a schedule, of sorts. Training happened once a week: Saturday afternoons, usually, unless we had a social obligation. Often it happened then even if we did have a social obligation, and there would be a sort of Pygmalion/My Fair Lady component, wherein I, Eliza-Doolittle-like, would have to display some particular, emblematic behavior in front of the world to demonstrate my progress.
In the stage I'm describing now, the stage that was nearly exclusively about my anus, I would invariably have to wear a butt-plug harness, usually under a skirt, or dress, with no panties. Putting on such a device in which to go out to dinner, or over to a friend's house for drinks, was an experience almost too delicious to describe--though of course I'll attempt a description.
First there was the insertion of the plug itself (not of course my "big trainer," but a much smaller one; as you'll see in a future episode, I couldn't walk without crying out when my big trainer was in my ass, not to mention that in the early days I had as yet managed to receive only about a quarter of it, and the remainder, remaining outside, would have been [understatement of the century] extremely awkward in any social situation, not to mention the car-ride to such a social situation).
(I should say that Charles was, as you'll see in a moment, more than willing to make me endure smaller, but still excruciating, moments of awkwardness in connection with my anal-training.)
I would shower, and get the plug, and the lube. With Charles standing, watching me, wearing his best Cheshire Cat grin, I would climb onto our bed and get on all fours. The plug I was usually assigned was a purple silicone one, of the standard elongated diamond shape. I would lube it up, and then lube myself. Then I would insert it, trying not to groan or whimper, so as not to give Charles the satisfaction. On the rare occasions that Charles was busy elsewhere, I would generally give myself a quick, furtive orgasm at this point. I think he caught me only once (and great was the resulting spanking!), though of course being caught was the point. More frequently, I was able to insert the plug in an alluring enough way that my husband couldn't resist climbing onto the bed himself and taking advantage of me. Sex with a butt-plug inserted isn't something I crave--it's just too much of a good thing, really--but knowing that I'm having it (that I'm being taken) because my husband couldn't resist the sight of me putting my butt-plug in is one of my top-ten favorite erotic things.
Then there was the harness, made of black leather. I'm such a white-lace sort of girl that having my pretty panties replaced by leather straps is always jarring. Charles spent a long time tracking down something that approximates what O wears at Roissy--the most important feature of which is the chains (straps, in my case) that run along the creases of the thighs, leaving the pudenda accessible to a Master's hand beneath the skirt.
Before we left the house, Charles would always bend me over the arm of the sofa, and lift my skirt. Almost always, he said, as he laid his hand on the flange of the plug, and pushed or pulled a bit to make me moan, "Charming." Often he would take a picture.
Once we were out in public, the various emblematic behaviors I would have to enact were all variations on the central theme of "My ass belongs to Master." There were things for me to do, and things for me to say. By the third such outing, the ritual was pretty well set: as soon as we were in the car (I was commanded to bring a towel to sit on, the very feel of which under my naked-but-for-the-harness bottom made me grow warm between my thighs at the shame of having to sit on a towel so as not to ruin the seat-leather of my husband's car with my arousal [and what if a friend noticed the towel?!]), I had to lift my skirt to my waist, and spread my knees, raising the right one so that Charles could move his hand from the gear-shift to my pussy and the butt-plug whenever he wanted to.
So he would edge me, on the way to wherever we were going. When we arrived, if we weren't late, he would park, and then, humiliatingly, bring me off there in the car, as I had to repeat "Natis mea tibi est, Domine," (My bottom is yours, Sir) three times as I came.
During whatever social activity we were engaged in, Charles, in the role of my trainer, would at any moment he chose move next to me and pat my bottom right where he knew the base of my butt-plug was concealed by my skirt or dress. Not only, with many dresses, did this clearly outline the back strap of my harness for all to see, but it also invariably made me gasp--sometimes in the middle of a conversation with, say, a friend of my Mom's.
When my trainer had patted me there, I was required to turn to him and whisper into his ear "Natis mea futuenda" (My bottom needs fucking).
Also, whenever Charles caught my eye and nodded slightly, it meant he was telling me to smooth my skirt behind me and thus to make the flange of my butt-plug momentarily visible in outline beneath it. I still have no idea whether anyone noticed--with the single exception of a high-school friend whom I would never have guessed to be kinky but who came up to me one night at the country club and whispered "Nice butt-plug, Emily; I'll have to show you mine some time."
Finally, towards the end of the party, or the dinner, or whatever, my trainer, at a moment when he was across the table or the room from me, would catch my eye, and raise his index finger, and give me a cuing gesture, as if to say, "You're on." Under penalty of the paddle, I had to put my hands on my bottom (even if I was sitting down, which always drew thrillingly embarrassing looks) and look into his eyes, and mouth the words, "Emilia tua cupit te natem suam futuere" (Your Emily wants you to fuck her bottom).
And then we would go home, and I would get my wish.
If you liked this little story, I'm pretty sure you'll LOVE the EXPLORATIONS Omnibus. Here's a taste:
"Now, I'm sure you know how to kiss a sister-wife, girls. Let's try again." With tears wetting our faces, we kissed again, managing to put on at least a bit of the girl/girl show the masked men seemed to be looking for. Then I felt the bed take the weight of first one, then the other, of the men. "Oh!" said Sarah, and I heard the wet sound of lube--and then I gasped as I felt myself getting the same treatment.
"She's nice and tight," said the talker, about me, I thought with a flash of pride.
"This one's looser--you can tell Smith uses her here pretty often." Oh, no. Sarah was the tight one--I was the ass-wife.