A Sissy's Progress - Chapter Five

A click of heels. A smooth rustle of fabric. And there she is, towering over me as I squat here in my pastel prison. "You're being such a good baby for me this morning, aren't you?" Erica coos, her fingers twining through my lengthening hair. "You've been working so hard, typing all those big words for Mommy..."

I nod mutely, gazing up at her momentarily before blushing and dropping my gaze. But she's not finished with me, of course. "Aww, so cute! Now, I can't have my little sissy baby getting all dried up," she chortles, and plucks the pacifier from my working lips. "Go on, suck on this instead," she orders - and my mouth is filled with the familiar, rubbery teat of my feeding bottle.

It doesn't take too long to down it. I've had a lot of practice suckling on things, you know.

And when it finally drains, gasping and squeaking between my moistened lips, Mommy smiles and pats my tousled head. "Good baby." She reaches down to lift my pacifier back to my lips, and I catch a whiff of her perfume. What a difference from myself - from my own unmistakable aroma of powder and lotion and a whiff of urine... "Now hush up and get back to work, baby. Mommy wants to read a whole lot more."

Well, there's not much else I can do, is there? And so, slipping down with an involuntary little burp onto my juice-filled belly, I begin to type once more.

***

I still remember that cool September evening  - that evening when I unwittingly sowed the seeds for the next step in my own humiliation. We were out for dinner together, Erica and I. We'd started a weekly dine-out tradition shortly after the whole Julie affair blew up. You see, previously Erica had been out with her girlfriends twice per week, shopping and drinking and god knows what else. Not that I had minded; after all, those were the evenings that allowed me to slip off and fornicate a bit on the sly...

But now that Erica knew what I'd been doing with all that free time, she had magnanimously offered to spend one of her evenings out with me instead. "It'll be some time together. To bond, you know. Maybe enjoy some nice food and nice wine, and just be a couple again. Doesn't that sound nice?"

So there we were after work on a Friday evening, seated together at this lovely, romantic Italian place. It might not have been a three-star Michelin place, but I don't think either of us cared. They had lots of pastas and pizzas and wines, and maybe because I don't really consider myself a food snob, I was enjoying every bit of it.

As we waited for our concluding tiramisu to emerge from the kitchen, I decided, naturally enough, that it would be a good time for me to excuse myself and find the men's room. All that wine was starting to flow through me, you see, and I'd never had the largest bladder. "BRB, honey," I told her quietly, and then slipped off to the toilets.

Oh, yeah. I forgot to mention. The cage was still on - and had been for maybe a week already.

I'd begun getting more accustomed to the unusual weight dangling from between my legs, but it still felt rather odd. At Erica's suggestion I'd switched from boxers to some nice, tight-fitting briefs; they were pretty thin and flimsy, but at least they helped hold up that silly cage and keep it from dragging things down.

Perhaps this is all TMI. But I'd also taken to using the stalls when in a public bathroom, and to sitting down to do my business. Sure, now it seems pretty silly. But knowing well how short the dividers in some restrooms were, I was mortified by the idea that some other bloke might sidle up to the urinal beside me and spot that odd pink plastic protruding from my trousers...

So as I finished up and slipped my khaki dress pants back into place, I winced as I felt a sudden spurt and trickle from my caged prick. Dammit. I missed being able to squeeze and shake and otherwise work those last drops out before tucking my dick back away where it belonged.

Well, there wasn't anything I could do about it, was there? And so back out I went to Erica and the tiramisu and the check, little knowing where that silly little dribble would lead...

"Honey." I turned, wondering why Erica sounded so amused. It was scarcely five minutes after we'd left the restaurant, and we were strolling down the darkening street on our way back to our Lyft pickup location. "Honey, what's going on down there?" I followed her smiling gaze down to my crotch. "Did you spill your wine or something? It's a little wet down there."

God, if only it had been wine. But I'd had a Merlot, so there was no plausible deniability there. No deep purple blotch - only dampness...

"Umm, I dunno," I mumbled. "I guess maybe I spilled a bit when I was in the bathroom..." "Spilled what?" Her tone was teasing as she slipped her arm around me. "Wait, did you wet yourself like a wittle boy? Hmm? Did my hubby just wet his wittle panties?" I must have been blushing redder than a tomato at her singsong banter. Damn, that wine must've gone right to her head. "Shhh, honey! It's not my fault. It's all because of-"

I drew up short, suddenly conscious of the dozens of other late-evening shoppers on the sidewalk around us. "Because of what, babe?" Erica was smirking openly now as she whispered, still far too loudly for my comfort, into my ear. "Do you mean to tell me that your new little toy is to blame for making you dribble in your pants?"

"It's just that- Well, yes, but- I mean-" I tried to explain as furtively as I could, but she didn't really seem to be listening to what must have sounded like a series of lame excuses. And minutes later, as we slid into the waiting Lyft, she was still grinning as though she'd just heard the best joke around.

"Oh, honey, that's so cute!" she whispered as we sped off into the night. "I'm sorry about it, really. But you have to admit, it really is kind of funny..." I sighed. "You think the strangest things are funny, hon. On the other hand, though," and here I slid closer, fired by a sudden burst of inspiration. "If you'd unlock it tonight, I promise you there'd be something very different from a dribble coming out - if you know what I mean..."

She pulled back in mock horror, then grinned deviously at me, the passing city lights glinting off her glasses. "Oh, really? Is my hubby that horny?" She slipped a hand tentatively toward my crotch, and I felt a pang as my deprived cock strained within its cage in anticipation. "No, wait..." And her hand withdrew slowly. Fuck.

"Don't want to touch those pissy pants of yours," she whispered in my ear by way of explanation. "But maybe, if you're really so horny..." She winked at me. "We'll see what we can do once we get home. Once we get you out of those wet pants, of course..."