Day by Day, Month by Month, Year by Year

“Day by Day, Month by Month, Year by Year,” Part 3
by c.w. cobblestone

August 1​

Ugh, this chastity device is killing me. I’m always aware of it because it tugs at my junk constantly and I stay horny. Even when I’m not thinking of sex, sometimes I’ll get an itch “down there” that’s impossible to scratch, and it’s frustrating as hell. That happened at work yesterday; I squirmed at my desk for hours, prompting one of the other lawyers to ask if I had hemorrhoids or ants in my pants. I told him my hip was hurting and that I couldn’t get comfortable.

August 4​

Molly’s foreplay with DeShawn lately has been to make me stand at attention at the foot of the bed while she does a sexy dance, shaking her ass and flaunting her tits in an effort to excite both DeShawn and me. When my dick swells, it pushes against the needle-like spikes inside my cage, causing pain so severe I end up rolling around on the ground in agony. Once I’m reduced to tears, they’ll kick me out of the bedroom and fuck. I guess I should be thankful that I’m at least a tiny part of her sex life, although it’s not easy adopting that mindset when all I can think about is how unfair and mean they are to me.

August 7​

Darlene came over for dinner tonight and flirted with DeShawn like crazy. After a few post-meal glasses of wine, the horny MILF started laying it on thick, telling DeShawn how hot she thought he was, and what beautiful grandkids he was going to give her. Of course, DeShawn ate it up and threw it right back at her, telling her she was “fine as hell, with an ass that won’t quit.” After Darlene left, he told Molly he wanted to fuck her mom. Since my wife would do anything to please her king, she told him she didn’t mind. “In fact, I think it would be kinda hot,” she said. So, now, they’re talking about how to broach the subject with Darlene. I can’t believe how decadent my sweet Molly has become since falling under DeShawn’s spell. It’s scary. She’s not the same girl I met just a few years ago.

August 9​

Molly invited her mother over for dinner Friday night “to have a little three-way fun with DeShawn,” and I had to run to the store to get groceries for this special occasion. DeShawn warned me not to mention any of this to his mother. Why, I don’t know — it’s not like the hateful old bitch has morals!

August 11​

I had to drop off a motion at the courthouse today and was petrified going through the metal detector, fearing my cock cage might set off the buzzer. My device is made of graphite, and the instructions said it would elude metal detectors, but that didn’t quell my anxiety as I approached the guard station. I sailed right through, although that didn’t make my nervousness go away. Fear is always in the back of my mind with this damn thing on. I’m constantly worried that I might get in an accident and doctors would have to strip me. Instead of the dirty underwear everyone’s mom warned them about, the docs would find me wearing panties and a medieval-looking contraption on my privates. Oh, well, if it happens it happens. I’m used to being embarrassed, WTF.

August 13​

Last night was a major turning point. DeShawn fucked Darlene for the first time, but it clearly won’t be the last time. I wasn’t allowed in the room but I could hear the moans. I spent most of the evening doing laundry, trying to concentrate on scrubbing out stains amid the sex soundtrack that blasted through the condo. Every now and then my dick would start to swell and I’d double over in pain. I was scared to death Molly and Darlene might require me to do cleanup duty after DeShawn was done fucking them, which would surely cause me great agony, but when the threesome was over, I was called to serve drinks and bring damp towels. I had mixed feelings that my tongue wouldn’t be put to use. The three of them lay around in bed watching TV the rest of the night. Darlene never looked so happy and Molly was beaming. They kept talking about making their threesome a regular thing.

August 16​

Violet was at Cassandra’s house when I came to clean last night after work. I had to show off my brands and cage, since Violet hadn’t seen them. She asked Cassandra if the cage meant she couldn’t kick me in the balls like she’d done last time. Cassandra said “let’s find out” and had me stand with my legs spread and hands on my head, naked other than my chastity device. They spent the next half-hour destroying my testicles. When they finally got tired I put on my maid’s uniform and started cleaning while they relaxed in the living room getting ***** on wine. It was difficult to walk because my balls were so swollen, although Cassandra told me to “stop limping around,” so I forced myself to stay upright, despite the throbbing in my groin. After a few glasses of vino, Violet made me drink her pee, taking the cup into the bathroom again before handing it to me and saying “there you go, faggot white bitch.” I thanked her, emptied the cup, washed it out and got back to my housework. Violet was still there when I reported to Cassandra that the chores were all finished. When I knelt in the hallway for my “goodbye” ritual, DeShawn’s mom changed things up a bit. After pissing in the cup, instead of making me drink it like she usually did, she dumped the contents on my head. By then, I’d changed back into my suit for the drive home, and now I’ll have to take it to the drycleaner’s tomorrow. Damn, that woman loves humiliating me. Must run in the ******.

August 19​

Darlene came over again last night and she, Molly and DeShawn disappeared into the bedroom for several hours. When they were done fucking they called for drinks and towels. There was a smudge on Darlene’s wine glass, so she picked up DeShawn’s underwear off the floor and arranged them on my head before berating me for being such a “wimpy little fuck-up.” It was embarrassing as hell, but I spent the night peeping through the leg-holes of DeShawn’s briefs with my nose in the crotch. Molly said in my maid’s dress and mask, I looked like a “sissy superhero.”

August 22​

I’ve got a pounding headache. DeShawn bitch-slapped me during dinner when he found a kernel of corn in his cognac, and my head is still throbbing. I guarantee the corn wasn’t in the glass when I served it to him; I’d made corn on the cob to go with the short ribs, and I’m almost certain the kernel fell into the drink while DeShawn was stuffing his face. That didn’t stop him from slapping me silly when he went to take a drink and encountered the offending nugget. Molly thought it was funny, although her mood changed when my nose started bleeding, and she yelled at me to go get a tissue. DeShawn really got me good — two hours later, the whole side of my head is still pounding. I try my best not to piss him off, but sometimes there’s nothing I can do.

August 25​

I ran into Joel and his wife Cindy in the supermarket yesterday. He couldn’t help making a smart-ass comment; when he saw the two cases of Corona in my cart, he says “I see you’re stocking up on your boyfriend’s favorite beer.” I just kept walking. Cindy called after me, “you’re pathetic, you know that?” but I didn’t reply.

August 28​

OMG am I exhausted. DeShawn had me go by his brother James’ house yesterday and serve as the gofer while he and his buddies repatched a roof. James isn’t as mean as DeShawn or their mother, but he still treats me like I’m scum, and ran me ragged for nine hours without one break. I felt so resentful watching them relax during lunch while they had me wash off all their tools. Everyone there knew the score — that I was DeShawn’s little bitch — and they weren’t shy about barking orders at me. At least James let me drink from the garden hose; had his bitch of a mother been there, I’m sure I’d have been provided a different, saltier beverage.

August 31​

Darlene spent the night and during breakfast I found out the hard way that she hates crunchy bacon. She had a bit of a hangover and was in a pissy mood, so when I set the plate in front of her and she saw what I’d cooked, she slapped the shit out of me, poured OJ on my head, and told me to fix her another serving of bacon. Aside from her crankiness, she seems to have picked up on the fact that being cruel to me makes DeShawn horny, and she’s been dogging me more than usual when she comes over. Like mother like ********.