The 7-Day Challenge Pt. 03


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Tuesday 30th, 9:30am

A text on my cellphone at from my sister Jennifer. “Lunch?”

I respond. “Sure. What up?”

“Need 2 talk 2 U about prsnal stuf.”

“OK. Auggie’s at 11:30?”

“OK. C U then. Luv U!”

My sister and I loved each other, sure, and we always knew – we never had to say it. Whatever the problem was, I figured it was serious.

Tuesday 30th 11:30am

Augie’s Haufbrau is an old cafeteria-style place where you go through the line with a tray, get your food, pay and then find a table. Hardly fine dining, but the lunch special was not a bad deal. You got a cheap steak, mashed potatoes, a few overcooked green beans and a soda for $5.99. It filled you up.

Jennifer had already gotten her food and was seated in a booth waiting for me when I came off the food line. I slid in opposite her and unwrapped my cutlery from the paper napkin they were rolled in.

“James, you look like shit,” she exclaimed when she saw the bags under my eyes. “You OK?”

“Yeah, sis, I only got a couple hours sleep last night. Got a lot on my mind.” I sliced up my steak and began to devour it. All that fucking will build up an appetite in a man.

“Well shit, brother of mine. Maybe you should knock off early to go home and take a nap.” Thankfully, it had been a slow day at the shop. I was exhausted; maybe I would do just that.

“Not a bad thought, maybe I will. But we’re not here for that. How are you doing? The kids OK?”

“The kids are fine, they’re with Claire.” Claire Rivers was Jennifer’s mother-in-law. She was about 10 years older than our mom Toni. She was short with long hair that was a kind of a silvery-blonde, but she always wore it done up in a bun. What I really loved was her cute face with that little turned up nose and a sweet smile that mirrored the incredibly sweet person inside her. I have to admit, I’d jacked off more than once fantasizing about undoing that hair bun and fucking that matronly body. I also loved how Claire adored Jennifer and the twins; she was definitely aces with me.

“Is it Alan? Is he mistreating you?” While his mom is the best, after more than 2 years of marriage I still hadn’t decided if I liked my brother-in-law or not. Jennifer had hinted in the past things were not always rosy between them, and from my point of view if you mistreat my sister, you and I got a big problem. (Ask her abusive ex-boyfriend Kenneth. I wonder how long it took for those facial bruises to fade.)

“Alan’s treating me just fine. The couple’s therapy seems to help a lot.” Hearing that, my respect for Alan went up a notch. But just a notch. “The thing is now, he seems to have a medical issue. You remember how Alan had some radiation treatment for pre-cancerous tumors in his small intestines?”

“Yeah,” I responded, “but the treatments got him back in the clear, right?”

“They did, but…” Jennifer reached over and took my hands in hers. She lowered her voice to a whisper. “The radiation may have damaged his sperm production. We conceived on our wedding night, it was so easy. But now I want another baby, we’re not able to!” Her hands grasped mine more tightly.

“How can I help, Jen?” Tears were forming in her eyes, which of course caused my cock to harden. Damned dacryphilia!

“Alan and I have decided we’re going to undergo fertility treatments to have another baby. Even though he’s got insurance through work, our co-pay costs are going to run $1,500 just for the preliminary tests. Our IVF costs might run over $10,000. Alan is a good provider for us, he works really hard, but he’s just a forklift driver. He only makes about $50,000 a year! I have my part-time job, but the cost of day care is already killing us.”

Anguish was crossing her face, and my heart ached for my sister. She took a deep breath, and then continued.

“James, I know you’re not exactly swimming in dough, and I wouldn’t ever ask you for money. What I need are ideas. What can we do to afford these treatments?”

I sat back and swallowed the piece of steak I’d been chewing. I had suddenly lost my appetite, and my meal had grown cold. I took one of her hands and I kissed the back of it. “Sis, don’t worry about it. Nobody knows this, not even Momma, but I got a thing I’m working on with my boss that may help us afford it. I can’t give any details, but just trust me, OK? And don’t say anything to anyone.” Jen nodded in silent agreement as she sniffled.

Tears were pouring down her cheeks now, and my cock was getting commensurately harder. ‘STOP it!’ my moral conscience shouted in my head, ‘this is your SISTER, damn it.’ My rational brain fired right back, ‘Funny thing to hear coming from a guy fucking the shit out of his MOTHER’. Breaking off my internal debate, I re-focused on Jennifer.

Using her napkin to dry her tears, Jen squeezed my hands again, gently this time. “Thanks, James. You’re the best. But enough about me. How’d Momma take the news about you and Katie?”

I stammered gaziantep escort to buy time to think of a response. “Ummm, well, yeah, you were right, Jen. Not too well. Not well at all. She wants a week to think about it. So, we’ll just wait and see how it goes!” Whew! Jennifer knew me too well, if I had lied she would have known right away. That was a truthful response; I just left out some details. Now it was my turn to ask questions.

“So Jenn, just out of curiousity, do you know if Momma is seeing anyone? I’m thinking if she had a boyfriend of her own she’d be happier and might not resent Katie so much.” What I DIDN’T say was I was hoping Toni could become emotionally distracted before I got in too deep with her. My heart wanted Katie; my cock wanted Toni.

Jenn thought for a minute. “There’s an older guy she met at work, Duane I think his name is. I think she goes out with him once in a while, mostly for company more than anything. They’re just friends.”

“You don’t think they, ummm…”

My attempt at tact made Jennifer laugh. “Get busy? Do the wild thing? Make like the beast with two backs? Bump uglies? Ride the old kielbasa? Oh, James, you slay me sometimes.” She had to catch her breath from her laughter. It was good to see he smile like that. “NO, James, Momma is like a fucking nun. I think if she did lay some pipe with the guy she might be more easy-going. I suspect her pussy’s got tumbleweed blowing through it right now. If you ask me, what she really needs is someone to drill her good and strike oil, get her all lubed up.”

The sight of Toni’s naked body covered with love bites flashed through my head. My cock got hard again before I could re-focus. I hoped my sister didn’t notice the lump in my coveralls. “Well, OK, thanks Jenn,” I responded, snapping back into reality. I wondered how long I could keep this challenge a secret from her.

We both got up, and I threw a few bucks on the table to tip the busboy. Jennifer hugged me hard, kissed my cheek, and whispered, “Thanks again, James. You’re the best brother anyone could ever ask for. I love you.”

Tuesday 30th, 1:15pm

My conversation with my sister left a suspicious hunch in the back of my mind, so on my way back to the shop I drove by Toni’s. There was a strange car in the driveway, a two-door late model Mercedes with a plate that read “D-WANE”. Something inside me snapped. I pulled over next to the curb and texted Roger that I wasn’t feeling good and was taking the rest of the day off.

Making my way in through the garage I picked up an aluminum baseball bat from my grade school playing days. Too small to play regular baseball, but big enough to knock a home run using someone’s head if need be.

I quietly crept into the kitchen. I could hear strange muffled sounds coming from upstairs. Slowly I went up, step by step, avoiding the creaky 4th and 7th stairs. (In high school, Jennifer and I had become experts at after-curfew sneaking in and out of this house.)

By the time I got to the top of the stairs I could clearly hear people fucking. What shocked me was the noise was coming from my old room! The door was slightly ajar, and I pushed it open a few inches more. Toni was on all fours on my former bed, and this Duane guy was pumping her from behind. Her ass cheeks were still red from the spanking I gave her, but that didn’t seem to faze him.

As Jen had said, he was an older guy, late 50’s I’d guess, with graying hair, a bald spot, and a ponytail. (I hate gray-haired ponytails on old guys; it’s like a revival concert for washed-up 60’s rock bands.) He wasn’t fat, but his body had spread to middle-aged thickness. There was nothing wrong with his cock, though. Based on what was coming out of Toni’s mouth, it seemed to be in perfect working order. I thought to myself ‘Yeah, right Jenn, Momma is like a fucking nun’. More along the lines of ‘Momma is fucking like a nun’, you mean.

“Oh, GAWD James! Fuck me harder, please!” My mouth dropped open when I heard this. His name was Duane! Why was she saying my name?

“Yes, Mommy” the guy answered answered. Holy fuck, he was role-playing me – in my old room!! How fucked up was THAT?

In a husky voice, she urged him on. “Take the condom off, James, I want you to come in me! Mommy wants to feel your hot sperm in her pussy!” Toni was really getting into it.

“Oh, YES Mommy,” he groaned, and pulled out of her pussy. As he reached down to remove the condom, I laid the aluminum bat on his shoulder. It was as if I’d hit him with a stun gun. One second he’d been a hot stud, the next second he was as unmoving as a marble statue in an art museum.

“You might want to rethink that,” I said quietly.

Toni turned around and shrieked “JAMES! What are you doing here!?!?!”, grabbing for a bedsheet to cover up with. She did a poor job of it, as the bite marks I’d left on her tits were very visible.

“Shut up, slut,” I snapped. “I’ll deal with you in a second.” I turned towards her pretend-James boyfriend. (Looking at the size of his tiny stiff cock, gaziantep escort sitesi he was truly a Mini-me!) “You need to get gone, and stay gone. The next time I see you with my mother this bat will be swinging, you got that?”

He exaggeratedly gulped like people do in comedy films, and nodded. I lifted the bat off his shoulder and he zoomed out like an Indy racecar on the final lap to the checkered flag. Didn’t even pick up his clothes, he just grabbed his boxers and was gone. I heard tires squeal, and looked out the window. He had his car backed out of the driveway in the time I estimated he’d make it out the front door.

Toni was huddling under the sheet now, curled in a fetal position. “I’m sorry, I’m sorry, I’m sorry,” she kept repeating in a naughty little girl voice. I pulled back the sheet, exposing her back and shoulders, then gently lay the aluminum bat on her skin. She shrieked, and began begging, “Please don’t hurt me James, I’m sorry, please don’t hurt me.” I was so fucking horny I could barely think straight.

Tossing the bat aside, I knelt on the bed and pulled her upright, facing me. I grabbed the back of her head and pulled her into a rough kiss. As I softened my lips, her tongue slipped into my mouth and her arms encircled me. We kissed like this, slowly and deeply, for a few minutes. I reached down and undid my pants, releasing my dick which was now hard as the aluminum bat I had just thrown down. It pressed against her belly, and I rubbed it against that lovely mommypouch of hers.

Breaking off the kiss, I pushed her backwards and spread her legs apart. Her labia were already moist and pink from fucking, and she moaned with pleasure as I began to stroke them with my fingertips.

“Let’s get one thing straight,” I said forcefully. “From now on, your mouth and your pussy are off limits to anyone but me. Any other man I catch trying to get a blow job or trying to fuck you will be in for a world of hurt. You want to go to a movie or dinner with DEE-wayne or anyone else, fine, but you need to ask my permission first, and make it clear that it’s going to be strictly platonic. Anything beyond shaking hands is my territory. I’m claiming your mouth and cunt as MINE. Understand?”

Ever have one of those experiences where your rational mind sits by the sidelines and watches while your emotional mind takes total control? This was one of those times for me. My rational brain knew what Toni was doing, but was helpless to do anything about it but watch the scene unfold.

“Y-y-y-es James,” she said quietly, happy tears forming in her eyes. “Only yours.”

I got into place over her, my cock in position to ravage her sopping pussy. “You’ve been very bad. Good mothers don’t fuck like whores. I’ll punish you later for being a whore. But for right now, you want my cum in you? Your wish is granted!”

I plunged into her savagely, and she cried out, “Yes! Fuck your bad mother! Fuck her hard!” She came almost immediately, within a half-dozen strokes. I left fresh bite-marks on her already-marked tits and her neck, and felt her clawing my back and shoulders. When we both climaxed together my own orgasm seemed to last an exceptionally long time, spurt after spurt after spurt. She may not have been fertilized last night, but today she had a good shot at it.

We collapsed in a sweaty heap, and after some light kisses both of us started to doze. I lay behind her, spooning, my hands acting as a human bra. My heart was all in a tumble. I was enchanted by the smell of her peppermint shampoo, her sweat, and the co-mingling of our love juices. Somewhere deep in the back of my mind, I remembered Jenny’s ex-boyfriend Scott accidentally grabbing Toni that one time; he had acted like it was a total mistake, but now I was sure it was no accident.

I breathed in those luscious scents again and caught myself wondering if Jennifer also smelled this way after sex, but I quickly suppressed it. My last thoughts before sleep overcame me were, “This is not how this challenge was supposed to go. Not at all.”

About thirty minutes later I suddenly woke, feeling Toni rubbing her ass crack against my cock ever so slowly, almost teasingly. “Mmmmmm” she murmured, as if she were dreaming. My hands were still cupping her tits, so I gently squeezed them and began to manipulate her nipples with my fingertips. She let out a slow groan of pleasure. Her eyes fluttered opened as I began to move my cock in the wet canyon between her cheeks.

She turned her face to me. “James, please kiss me,” she whispered, and our lips met in a passionate lock. Her tongue invaded my mouth as my member regained its flagpole status. I slipped into her juicy pussy, and it made a slurpy sound. I slowly began to move in and out, but she broke off our kiss and pressed her hands to my hips to stop me.

“You know, there’s one hole you haven’t had,” she said seductively. “If you really want to claim me, you’d better take all of me. Otherwise, Duane might still have an opportunity. And you wouldn’t gaziantep escort tanıtımları want that, would you?” She giggled then, and it made me feel like a humiliated cuckold.

“Why you little tramp,” I said between clenched teeth, rolling her onto her stomach. “You’d do that, wouldn’t you? Just to make me jealous.” Pressing the head of my cock against her throbbing rosebud, I could feel her puckering and un-puckering the sweet sphincter, inviting me to take it.

“Feels like you’re already jealous, darling. Go ahead, take my asshole – unless you’d rather my boyfriend did it.” That pushed my buttons big-time, and I used my knees to roughly force her legs apart and lifted her hips up to give me better access.

With a great deep-sounding roar I began to push into her. She gasped, but with the ease it went in I could tell she was no anal virgin. Enough love juice had seeped out onto her crotch that my member slid right in, allowing me to fuck her ass in earnest.

At first she just grunted and moaned, but as I continued she spurred me on with her dirty talk. “NO! How dare you! You’re fucking your mother’s ass! Stop you bastard! This is wrong, this is incest. How can I tell my boyfriend that I cheated on him with my son’s big prick?” As her filthy diatribe continued, she kept pushing back against me, the fingers of one hand desperately rubbing her clit.

Soon I came hard, and collapsed on top of her. She lay trapped under my body weight, with my now-softening cock in her rectum.

“I’m officially all yours now, James,” she said. I could hear the happiness in her voice. “You’ve claimed every hole. What will you do with me?”

Before I could answer my cell phone alarm set to go off at 4:30pm went off right on schedule. I tried to extricate myself from Toni, my soft cock making a wet noise as I pulled it out of her asshole. I thought given the right physical persuasion, I could go one more round with this sexy beast. Instead of trying to seduce me again, she stretched and sleepily smiled and said, “You need to go to her. Keep up appearances. Make her think she’s got a chance. I’ll see you again at midnight.”

Toni began to roll onto her side away from me, but I quickly put my hand down and slipped my thumb into her juicy pussy and my forefinger in her very warm asshole. She squeaked, and her eyes went wide. I bent and kissed her deeply, threatening her in an low voice, “Remember what I said. This is my territory. Nobody else’s.”

I pulled my sperm-and juice-coated fingers up to her lips. “Yes, James, it’s all yours,” she whispered, then sucked my fingers clean.

I got up and took my shower. I didn’t want to be late for Katie.

Tuesday 30th, 5:30pm

With my mind fresh from the nap and my body clean from the shower I should have bolted up the steps to Katie; instead I was trudging. My emotions were in a whirl, my thoughts jumbled, and my body weary. I had changed into street clothes, my coveralls were in my messenger bag slung over my shoulder.

The door was unlocked. I went inside, and Katie leapt on me, kissing me frantically. “James, my love, I’ve missed you so much.” Adorable as always, she was dressed only in one of my dress shirts. It was unbuttoned and open, and the sway of her big tits behind the fabric was intoxicating. Nice…

“How did you manage to get one of my shirts?” I asked. I wear them so seldom I didn’t notice one missing.

“Before you asked me out the first time you had dropped it off with a bunch of other stuff to get cleaned. I had such a crush on you but you hadn’t noticed me. It smelled like you, so I kept it and took it home. That way I could wear it pretend you were with me.” She started blushing, a light red in her cheeks.

The dawn of comprehension came slowly, but then… “You STOLE it? Katie, I’m impressed! Now what else did you do while wearing that shirt,” I asked. “Were you naughty in it?” Now Katie blushed a deeper red, and smiled in a conspiratorial way.

“I may have touched myself ‘down there’ a time or two,” she admitted, then threw her arms around my neck and gave me a deep kiss. “You’re so adorable, do you blame me?” I just laughed. My good girl really COULD be bad!

She wiggled her huge tits against my chest and threw a cute little pout at me. “I came by the shop this afternoon to see you, but you weren’t there!”

“I had lunch with Jennifer, then I went home and took a nap,” I lied. “Besides, seeing me in the afternoon is against the rules of the challenge, you know that. It wouldn’t be fair to Toni for you to have afternoon sex with me in the workshop, now would it?” Katie giggled, but I felt like a real shitheel for saying it with Toni’s cries of ecstasy echoing in my ears from this afternoon.

“No, it wouldn’t be fair, but it would be fun. I may try it again later this week, you never know!” She giggled again, and began unbuttoning my shirt. She was suddenly dead serious. “I told you James, you’re my man. I’d lie, cheat, and steal, anything for you. When I say anything, I mean anything!”

“I’ll hold you to that,” I said. Again, my mind was reeling from the implications. My shirt now undone, she pulled it entirely off as we headed into the bedroom. Once in the bedroom she was at my belt buckle, unzipping my pants and pulling them halfway down to expose my cock, stroking it to hardness. I wanted her mouth on it, but I would not force her.

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