Day by Day, Month by Month, Year by Year

“Day by Day, Month by Month, Year by Year,” Part 5
by c.w. cobblestone

October 1​

When I returned home from work today and got the mail, I was surprised to see a package with my name on it. Inside was a giant strap-on dildo. Molly laughed at my shocked expression and told me she’d ordered it because her mom wants to use it on me the next time she comes over for a threesome. I had to call Darlene to thank her. She chuckled and said, “no problem, I can’t wait to put you in your sissy little place. That’s why I had Molly order the biggest one they had.” That fucking thing is huge — my poor ass is going to be ripped to shreds. WTF. My mother-in-law is such a bitch.

October 3​

Today, I ordered the matching watercraft for DeShawn’s birthday. They’re scheduled to deliver them to the marina Tuesday, and Molly will take DeShawn down there on his birthday to surprise him. Not that the arrogant bastard will ever say thank you.

October 5​

Darlene just left and I’m in screaming pain. My asshole’s completely blown out after she drilled me with that behemoth of a dildo. The bitch was TRYING to make it hurt. She succeeded, and DeShawn thought my cries of agony were hilarious. But it could be a whole lot worse. I can thank Molly for my blessings, and despite my throbbing bunghole, my heart is throbbing, too. I love my beautiful wife so, so much! Tonight, she showed me that she DOES care about me! After DeShawn had me serve as his “ass-to-mouth bitch,” and everyone had enjoyed their orgasms, Darlene donned the strap-on and told me to bend over the bed. She initially had planned to fuck me with no lube, but my darling wife intervened and said that would likely tear up my insides and put me in the hospital. Darlene wasn’t happy, so she took her frustrations out on my ass. I can deal with the pain, though, knowing that Molly prevented further misery. Even if it was for selfish reasons, she didn’t want me going to the hospital. That’s something to be thankful for. Right?

October 8​

Ugh, I’ve got a major headache. I was giving DeShawn his propers about an hour ago, pretending I was licking Molly’s pussy, and I guess I got a little over-excited because he cuffed me across the ear and said “slow down, bitch.” That knocked me right back into reality, and my head’s been pounding ever since. My wife’s boyfriend likes slow, respectful licks. I need to remember that from now on, or I’m going to get brain damage from all the blunt force trauma. DeShawn hits hard.

October 10​

I was on my hands and knees cleaning the hallway baseboards earlier today while Molly chilled in the bedroom talking to her friend Alyssa on the phone. I could clearly overhear my wife’s part of the conversation as she brought up a recurring topic — how badly she wants DeShawn’s babies — and she laid out details of what’s to become my future. I’m still reeling from it. Nobody bothered telling me any of this stuff, and having to hear it second-hand like that while Molly chatted with her bestie is a supreme insult, even to a loser like me.

Still, the future doesn’t look all that bad. Well, some parts don’t, anyway. Some parts are terrifying. It’s a mixed bag, I guess.

Molly told her friend I’ll start wearing more sensible maid’s uniforms after kids are in the picture, rather than the sissified outfits DeShawn insists on now. I’ll also have to come out full-time as a transgender, including at work, so the kids will see me “as sort of a trans uncle who supports the ****** and then comes home to do the housework.” While it’s going to be embarrassing as hell having to tell all my friends at work that I’m transgendered it shouldn’t pose a problem professionally, since two other attorneys in my progressive firm have come out as trans during my 15 years there and nobody batted an eye.

According to Molly, DeShawn is completely onboard with me staying on as the ****** maid, although she told Alyssa, “he’s real funny about doing kinky stuff in front of kids,” and she said we’d have to tamp down our lifestyle a great deal. “He becomes so mature whenever we discuss having a ******,” Molly gushed. She wasn’t lying. I’ve been privy to these conversations, and it does appear that DeShawn is embracing the notion of fatherhood. He keeps saying how he wants a legacy. Of course, hearing that makes me feel like shit. But knowing that he's okay with me staying on gives me some measure of comfort — as does the prospect of losing the more extreme elements of our lifestyle so that Molly and DeShawn’s children can grow up in a somewhat normal environment.

No matter what happens, and no matter how big their household gets, I know I’ll always occupy the bottom rung. And having to come out as trans is going to be absolutely mortifying, and will surely push my former friends and ****** even further away.

But it would be nice to be free of the gratuitous cruelty DeShawn and Molly mete out daily. I’m sure they’ll always find opportunities to torture and humiliate me, since that’s a core element of our dynamic. And there’s no question Cassandra and Darlene will continue making my life miserable when I go to their houses each week to clean.

All in all, though, this plan doesn’t seem so bad. If things go accordingly, by coming out as trans I’ll trade public embarrassment, which I have to endure anyway, for better treatment at home. And the bottom line is, I’ll get to remain in Molly’s life. And that’s everything to me.

Still, if this is to be my future, I wish someone would have the courtesy to tell me about it. I guess they’ll get around to it eventually.

October 12​

Yesterday was DeShawn’s birthday, although I spent the evening at Cassandra’s house cleaning. Thankfully, I was alone, since Cassandra took her son and Molly out to eat and celebrate. I worked as fast as I could, hoping to finish my chores and get the hell out of there before Cassandra came home. I was successful, thank goodness, and for once I left her house without a bellyful of piss. When I got to the condo, DeShawn never said thank-you for all the gifts I’d bought, but that wasn’t a surprise. He was in a good mood, so as I gave him his propers while he watched the Celtics-Warriors game, I counted my blessings.

October 14​

I swung by James’ house after work last night to mow his backyard and carry a bunch of boxes from the garage to the basement. When I asked him if he needed anything else before I left, he snarled at me and spit in my face before telling me to “get your sissy white ass the fuck out of here.” DeShawn’s brother usually isn’t like that, so I was shocked. On the drive home, all I could think about was whether James had simply been in a bad mood, or if I’d done something to displease him that would’ve caused him to give DeShawn a bad report about me. My fears were unfounded, though, and DeShawn was chill when I got home. He even let me hit his blunt after dinner. It was good weed that knocked me sideways, and when I gave him his propers while he and Molly relaxed in bed watching TV, my mind did loop-de-loops. The phrase “DeShawn is my king; DeShawn is my king” played over and over in my head as I buried my nose in his ass, reveling in a buzzed world of abject submission. Now that the weed has worn off, I’m ashamed of myself. I’m supposed to hate licking DeShawn’s ass. Last night, I didn’t hate it at all. Fuck. What’s wrong with me? What am I turning into?

October 16​

DeShawn had me give him his propers while he watched the World Series last night, and I couldn’t get the phrase “DeShawn is my king” out of my head. On top of that, I started to get turned on, and yelped when my dick swelled and the spikes in my cage poked flesh. My outcry earned me a slap upside the head from my king. I mumbled apologies into his bunghole, went into “the zone,” and repeated the phrase “help me Obi-Wan Kenobi, you’re my only hope.” It didn’t help, and my dick got hard again, although this time I was able to stay quiet. WTF. Now I get turned on by licking that sonofabitch’s ass? I’m thinking this the Stockholm Syndrome at work.

October 19​

I’m exhausted. I’ve spent the last three nights after work painting Alyssa’s house. Each evening, I’d paint until about 11 before rushing home to clean the condo. Alyssa didn’t help at all. Instead, she relaxed with her dickhead boyfriend Todd each night and watched me paint. The first night, Alyssa made me lick her toilet in front of her boyfriend. He wasn’t amused, and told me “I ought to kick your nasty faggot ass.” Todd doesn’t go in for “all that sissy shit,” and he says I disgust him. He doesn’t mind exploiting me for my labor, though. I just try to avoid the asshole; I can tell it wouldn’t take much for him to lose it and beat the shit out of me.

October 20​

Since painting Alyssa’s house made me miss my weekly spruce-up at Darlene’s place, I’ll have to swing by there after work. I’m dreading it. Molly says her mother ordered a strap-on dildo to keep at home for when I come over to clean. She said Darlene promised to “be good and use lube,” but I’m guessing my bitch of a mother-in-law won’t be overly generous with the KY Jelly. WTF. So, now, I’ll have to get pegged after cleaning Darlene’s house, in addition to having to drink piss as payment for my maid service at Cassandra’s. I get no respect.

October 21​

Well, there’s good news and bad news. The good news: When I got to Darlene’s house last night, she told me the strap-on hadn’t arrived in the mail yet. The bad news: She improvised and reamed my ass with a broomstick. She says it’s a “power rush” fucking me like that, and that I’d better get used to it. She sodomized me as soon as I got to her house, so I spent the rest of the evening limping around as I cleaned while she relaxed in her La-Z-Boy with a smirk on her bitch face.

October 23​

Molly and DeShawn finally sat me down tonight and explained what they had planned for the future. I acted surprised and made sure to thank them for wanting me to stick around to serve them and their children. The one thing I wasn’t ready for was DeShawn telling me I had to come out as trans immediately. I thought they might wait until Molly got pregnant, but DeShawn says we might as well get started on the life we’re going to lead.

He told me since my name is Lou, he and Molly had thought about calling me Louise. But DeShawn said “Mildred” is a better name for a maid, so I’ll be “Mildred” going forward. DeShawn says I need to go to the County Building to get my name formally changed.

“When we start a ******, I don’t want no funny shit,” he warned me. “In front of the kids, I just want you to be the maid, that’s all.”

Molly added with a giggle: “You’ll be like Alice on ‘The Brady Bunch,’” she said, and she told me to order a few powder-blue uniforms similar to those made famous by the iconic TV domestic.

Although I kept my mouth shut, I snickered inside at the prospect of becoming the beloved ****** maid. Like that’s ever going to happen! I doubt Mike Brady ever forced Alice to give him his “propers” after the kids went to sleep, and there’s no way DeShawn would ever forego that perk because he enjoys it too much. I’ll still be “DeShawn’s little sissy bitch” — we just won’t do anything over-the-top in front of their kids. I’m sure it’ll be just peachy for me. Ugh.

Now that the prospect of coming out is at my doorstep, I’m absolutely petrified. Since Molly and DeShawn had “The Talk,” I’ve felt on the verge of throwing up. Tomorrow is Saturday, and Molly told me she’s taking me clothes-shopping. Later on, I overheard her chatting on the phone to Alyssa, who apparently will be joining us tomorrow, although of course, my wife never bothered telling me that.

After Molly and DeShawn went to bed, I spent more than an hour in the guest bathroom staring at myself in the mirror, crying like a baby and saying goodbye to the old me. It was a traumatic experience.

October 25​

Yesterday was pure hell. Molly and Alyssa led me from store to store, giggling like schoolgirls as I tried on what must’ve been a hundred outfits. I had initially dressed in men’s clothes for the excursion, since the only female stuff I had at home were my ridiculous maid’s outfits. But after our first stop, where I bought several dresses and skirts, I was made to don a polka-dotted dress for the rest of our shopping trip, marking my first public foray in drag, not counting the two times I’d served at DeShawn’s friend’s parties. Sure enough, I ran into my sister-in-law Cindy in Charleston Mall. She threw up her hands and said “you gotta be fucking kidding me” before storming away while dialing her cellphone. I’m sure she was calling Joel to tell him about the latest depths to which I’d sank. You’d think I’d be used to being a public fool by now, but each new humiliation feels like the first time. Anyway, I got through it, and now I have a female wardrobe. The “Alice” maid’s outfits should arrive in the mail next week.

October 26​

DeShawn told Molly he wants her to buy a sexy Halloween costume to wear to a party one of his friends is throwing Thursday. He said he may have me wear one of my flouncy outfits to provide maid service, although he said he needs to see if his friend is cool with it. So, in addition to being scared to death about coming out at the firm tomorrow, I’ve got that to worry about, too.

October 27​

Work was a nightmare. I could tell Mr. Berkowitz was surprised when I showed up wearing a blue business suit, makeup and heels. My hair hasn’t grown out yet, so I’m clearly not a woman. Still, the Senior Partner said nothing, and made sure to ask questions like how I wanted to be addressed. It was hard to talk, but I managed to tell him my new name was Mildred Katz, although I still use he/him pronouns. My coworkers had mixed reactions. The guys seemed amused, while the ladies were more sympathetic. Mostly, they ignored me, and I could tell they felt uncomfortable the few times we interacted. Jane, the one transgender who’s still at the firm, was friendly, and told me I may encounter problems with clients, although thankfully most of my job entails behind-the-scenes work like writing documents.

October 29​

I was giving DeShawn his propers last night when his friend called to say he didn’t want me to serve the party tomorrow. Apparently, his friend’s cousins are in town from LA “and he says they don’t play no fag shit,” DeShawn said. I breathed a sigh of relief and continued with my rim-job. Even lowdown fags like me deserve a break once in a while.