A Sissy's Progress - Chapter Twenty

"Ooh, that was a nice one, baby! I was getting wet in there just reading it." Mommy's voice is suddenly in my ear, and I start within my straps. "I think you've had more than enough time here now, though. So let's get you down and have you work a bit more in the living room."

Sure, I guess. I mean, I'm more than relieved to have that feeding gag slip out of my mouth and for the confining straps to allow me to slither to the ground. I trundle mutely off to the living room, there to find a blanket and pillow and my familiar pink pacifier awaiting me. It makes quite the contrast with Mommy's grownup home office in the corner: all mahogany and leather and steel, with elegantly curved screens and pin-neat organization.

No time to whine about how infantile my workspace is, of course. I grasp my pacifier and tuck it into my mouth, where my lips set once more to work. It really is curiously comforting in its own way, you see. And after all, even if I tried to go without it, Mommy would be along any minute to stuff it into my mouth with a condescending giggle and a smack of my rear...

And so I set to work on the next chapter: chapter twenty, the chapter in which I describe how I began to slither even further downward into the morass of sissified humiliation my loving wife had set up just for me...

***

"I've always wanted a baby, Shane, and you know it," Erica retorted that next morning. "So I suggest you simply get down off your stupid high horse and realize exactly how things stand. You've shown yourself incapable of being a faithful, strong husband for me, and we both know it. We've made some changes to accommodate that fact. And now I think we're both seeing just how much better off we are when your main focus is, well... pleasing me. Now don't tell me you didn't have fun last night?"

I flushed where I lay prone on the bed, my humiliation at even discussing her treatment of me the night before heating my cheeks. "Erica, I'm not- I mean, I'm sure we both had fun. It's just that I'm- I'm tired of-" "Of what, baby? Of realizing just how much better off we both are when you're my little one? Of admitting to me just how nice it is to let Mommy take charge?" "No- I mean, it's not-" God, why did she always have such a way of turning my words on their head?

But Erica just shook her head and taped my final diaper tab closed over my freshly caged cock. "I think I know what your problem is, baby. It's that toxic masculinity we hear so much about. You've been taught all your life that there's only one way to please a woman, haven't you? You've never even dreamed that there are other ways to bring her pleasure: to allow yourself to relax, to let her lead for once..." She chuckled and pulled me upright. "It's hard to overcome, I know. But if we're going to stay together, Shane, you're going to need to learn all those things..."

Her words and those memories of the night before wormed their humiliating way through my mind for days afterward. You see, I'd been diapered, dressed in women's lingerie and a frilly diaper cover that looked more likely to belong on a six-month old girl than a thirty-something man. And even despite such appalling treatment, I'd actually cum like that: hard and fast, all while babbling about how I was my wife's good little sissy baby...

I was slipping far, far below what anyone would ever have thought a man like me should be. Yet what could I do? Erica remained firmly in charge of my home and my sex life, and I wasn't about to push her any further for fear that she'd follow through on her threats to divorce me. I did still want to make her happy, strange as it may sound. And well, if that happiness came at the expense of my dignity in the bedroom... So be it? Question mark?

Yes, so be it. Because only two nights later, I found Erica once more removing my cage and inviting me to enjoy the mind-bending pleasure of the wand... as long as I donned that frilly diaper cover once more and suckled her breast while she relentlessly praised me for being such a good baby. Of course I did - for if you think I'd turn down another chance to relieve my aching blue balls, you clearly don't know me by now.

It wasn't long after that Erica voiced her next brilliant idea. "Shane, I know it's been hard for you to accept how much I love our new bedroom game." "Game?" I repeated, spooning a bit more mashed potato onto my plate. She giggled. "Oh, you know! It's just so much fun to play that you're my cute little baby..." I sighed. "Yeah, yeah. I know. I'm still not really comfortable-" "I know, baby," she cut in. "That's where I'm going with this. You see, I think you just need a nice little reminder of how much I adore my sweet little baby, and how how fun we have like that..."

Turns out the reminder she had in mind was pretty tame. You know, just a pink A-line undershirt and a switch to some all-pink diapers. Nothing that couldn't be covered up by my work clothes, as she so rightly pointed out. And it did seem to make her happy when I wore one or both, so...

Oh, yeah. Did I mention that I was now waking up more days than not with a swollen wet diaper under my pajamas?

I still don't know whether her next innovation was intentional or simply a happy accident - pun unintended. It was around the end of February, I guess, when I developed one of the worst skin rashes I'd ever had. You can probably guess exactly where it was located, too.

"Oh, Shane, this diaper rash looks awful! We'd better get you some cream or something ASAP." Erica was good as her word - and before twenty-four hours of itchy, painful hell had passed, she'd gotten her hands on not one, but two creams to help my poor flaming ass recover. I'd thanked her, of course, though the irony of me thanking her for helping alleviate a condition brought about by her own insistence that I remain in diapers was not entirely lost on me.

The creams, puzzlingly labeled with terms like estroven and progesterone, worked wonders. As a result, it wasn't long until Erica was applying them liberally with every diaper change: you know, just as a preventive measure. Another preventive measure she soon adopted, though, and one that I pushed back on as hard as I dared, was a bit more... well, drastic.

"Shane, you know this only makes sense if we want to keep you from getting rashes. Hold still now, or you'll get a cut!" Yes, Erica was shaving my freshly showered nether regions. With a safety razor and shaving cream. While I craned my neck up in growing dismay. "Look at that - just like a sexy porn star!" she teased as she finished, probably trying to allay my vocally expressed misgivings. "Honey, you look just great now. It's practical, it's sexy, and, well..." She giggled. "I actually think it suits you just fine." She left unspoken the thought uppermost in my own mind, though I have no doubt she shared it also. Smooth, just like a baby. How... fitting.

The final innovation was even more invasive, though. "You know, I've been thinking," Erica murmured one night after another frenetic bout of wand-fueled orgasms. "You've never tried anal, have you?" No, I had not - and, I was about to say, I had zero intention of doing so. "I hear it can be absolutely amazing for folks who prefer not to use their dicks," she ventured. "And you know, I'd be more than happy to give it a try. I do want you to be happy and satisfied too, you know..."

Oh, did she? Well, I wasn't about to question her on that particular point. But it couldn't hurt to humor her a bit... right?

I still remember that evening when my half-nude wife first produced the rubbery, flared lozenge with which I was about to become intimately familiar. "We'll just give it a try tonight, okay?" she cooed, running her lube-slick fingers up and down its length in preparation. "And if we don't like it, we don't have to keep on - I promise. Now spread those legs for Mommy, baby. Yes, nice and wide. Now just relax..."

I don't know if I should be ashamed to confess it. But honestly, that combination of an uncaged dick, a plugged ass, a diaper, and a naked wife coaxing me onward with her vibrating wand sent me reeling into orbit.

It was only after I came down from that glorious high that she giggled softly in my ear. "My, my. Look at my good little sissy baby enjoying his plug! I bet you're going to love wearing it to work tomorrow. And it's going to be so practical, too, keeping you from making a stinky in your pampers..."

Unfortunately for me, I was still too euphoric to care at that point. If she wanted to tease me and humiliate me, so be it. But right now, the orgasms made the whole humiliating charade worth it.