The 7-Day Challenge Pt. 01

This is my first story on Literotica. Thanks to my coach, Carnevil9!

James wants to marry his girlfriend Katie. His Momma thinks Katie's not good enough, and challenges her to a 7-day long contest, the prize being possession of her son's heart (and other parts)!

*****

Tuesday, May 23

"It's a mistake, James. No way will Momma accept it. Just elope and be done with it." My twin sister Jennifer looked across the table at me, her soup steaming in front of her. We had met for lunch at a local café. Jen has always been my best friend and confidant, so of course I had to ask her advice about my recent engagement to my girlfriend Katie Farmer.

Our momma Toni Barnett had raised us alone from the age of 3 after our daddy Eddie Barnett took off; she was no more than a child herself because they eloped when she got pregnant at 14. Many times Jennifer and I had to fend for ourselves while Momma worked. We were a team.

Jennifer and I are twins, 22 years old. I'm brown-haired, fair skinned, slim and 6' tall like my daddy. Jennifer is also fair skinned, but 5' 7"tall with more of a solid build and red-haired with freckles like our Momma, who's 36. (Not fat, just solid, about 160 pounds.) Both had C-cup boobs. Jennifer looks so much like Momma that one time her boyfriend Scott, snuck into the kitchen where Momma was doing dishes and grabbed her from behind, his hands holding her boobs while rubbing his crotch against her butt. Boy, there were two red faces when he discovered his mistake. Jennifer dumped him right after that.

Momma confided in me that she had half a mind to call Scott herself, as she had actually enjoyed it. I don't know if she ever did, but we never saw him again.

"Come on, Jenny. It would be disrespectful not to ask Mom for her blessing. Plus, she'd go ballistic if we eloped! That's what she and Daddy did!"" I was surprised at my sister's response.

"Look, James, we both love her so much, but I'm telling you Momma won't go for it. You and she are just tied too strong. You've always been her favorite, probably because you remind her so much of Daddy." I couldn't argue with Jen. Momma had unconsciously made it clear in many little ways, and one time in a big way!

Sometimes I'd see her looking at me in a dreamy way, a funny look on her face. She never got over the devastation of Daddy leaving her. When I was 18, Momma learned he'd remarried and she went on a 3-day bender, drunk for three days straight. On the third night, unbeknownst to me she mistakenly crawled into my bed. When I walked into the room she spoke to me as if I was Daddy.

"Come here, Eddie," she slurred, "I wanna suck your cock." She reached for me, trying to pull my pants down, but was so drunk she ended up falling out of bed. She was mostly dead weight, so picking her up to put her back in bed meant a lot of bodily contact. Her tits came completely out of her nightgown, and I got handful of ass and boobs as well as a good look at her luscious huge nipples. My cock became involuntarily hard, springing out of my pajama bottoms. Like a blind squirrel finding an acorn in the forest, her hand found it. She giggled. "See? You still want me, you fucking bastard!"

Drunk people can be quite strong. With her other hand she pulled me off-balance so I landed on top of her. Her breath smelling of whiskey, she whispered in my ear as she rubbed her crotch against mine. "Come on baby, my pussy's still hot." My mind was saying "No" but my overly-stimulated 18-year-old cock was saying "Yes." She put her lips on mind and her tongue in my mouth, so with conflicting emotions I proceeded to dry hump her. Being 18 and incredibly horny, I shot my wad on the crotch of her nightgown in about 20 seconds. By then she was passed out cold, so I got up and slept on the couch.

When she sobered up, she asked me, "Jimmy, when I was drunk I had the funniest dream. I dreamt your Daddy came back. I mean I think it was a dream, but it was so real. Did I do anything funny while I was drunk?" I told her all she did was cry in her sleep, (which she did later), but assured her nothing more.

"Thanks, baby," she replied. "You were always such a sweet and good boy, and you've turned into a good and handsome man."

Months later, while I was helping with the laundry when she had the flu I found her nightgown with my dried cumstain stain intact, folded up neatly in her bottom dresser drawer. I sniffed it and immediately got hard knowing it was there, and unwashed as well.

I was daydreaming about that incident when my sister's voice broke my reverie. "James, are you listening to me?" I blinked back into reality.

"Sorry, Jen. Go ahead, I'm listening."

"The other thing is that your little Katie is extremely hard-headed, just like Momma. I look like Momma and all, sure, but personality-wise those two are practically twins. They'll butt heads from the get-go. Go buy a helmet, 'cause you're going to be the filling in a brick sandwich when they go at it. If you want to do this, you'd better prepare yourself for a hell of a battle."

I thanked her for her advice and she went to pick up her kids in kindergarten while I went back to my job as a mechanic at a bike store. Little did I know how accurate her prediction was, but I was soon to find out.

Sunday May 28th

My fiancée Katie is 5'1" and long blonde hair, with a tiny skinny body and disproportionately large D-cup boobs. She works at DreamKleen, the dry cleaners next door to The Country Pedaler, which is the bike shop where I work. I could just wash my work coveralls like any ordinary mechanic, but started taking them to be dry-cleaned when I saw the cute girl behind the counter. We struck up a conversation one day, started dating, next thing you know a year later we're engaged.

Katie is very religious, however, so we haven't actually fucked - she's been saving herself for marriage. But she has no objection to us making out and me playing with her titties, so we do that a lot. I just have to jack off to relieve myself after I get back to my apartment.

We have modest plans - I want to eventually buy into the bike shop where I work, and Katie is going to State College to finish her nursing degree, so she's in no hurry to have kids. I'm cool with that, although as an uncle I really enjoy spending time with my sister Jennifer's twins. (Twins run in our family.) Sometimes, it makes me want to have my own sooner rather than later.

Katie and I went to Mom's house for dinner. Immediately, I could sense a coolness between them. They were civil, but in that kind of way that masks underlying hostility. Dinner was great, Mom can really cook, and Katie had brought a really tasty gourmet salad. Typically I'm a what-beer's-on-sale guy, but because it was a special occasion, I had brought three bottles of what was, for me, an expensive red wine - $25 a bottle!

The three of us were two bottles into the meal when, after clearing away the dishes, I broached the topic. "Momma, Katie and I wanted to get together with you to let you know we're engaged. It's kind of old-fashioned, but we want your blessing."

Momma looked at us, and said one word: "Bullshit."

Katie and I looked at each other, shocked. "Momma," I said, "we're not kidding. We want to get married."

Momma opened up the third bottle and poured herself a huge glass, then downed half of it. "I know you're not kidding, James. But the idea of you marrying this little gold-digger is what's bullshit. Once she's got her hooks in you, you'll be screwed. She's not right for you, and you'll end up miserable. I won't stand for it."

Katie and I sat there stunned. Jennifer tried to warn me, but I was still taken aback at the vehemence of my mother's objections. Katie recovered first. "Why you dried-up old bitch," she retorted. "I'm no slutty gold-digger, I'm just a student trying to become a nurse."

Momma fired back, "James has worked his ass off to build his reputation and save up money to buy a partnership in the Country Pedaler. You, meanwhile, work a part-time job with no benefits in a dry cleaners and have nothing except the clothes in your closet. You forget I'm friends with your boss Maria at DreamKleen. She gave me the lowdown - you're no slut, I will grant you that, but you DO have a car loan for $14,000, $11,000 in credit card debt, and $25,000 in student loans at the moment. The minute you and my boy get married that $50 thousand becomes HIS debt as well, and it will flat out kill his dreams."

I looked at Katie in shock. I was so in love I had never thought to discuss finances, and had no idea how much debt she carried. To afford to buy into the bike shop I had been very frugal, and had saved as much as I could of my salary. I had only one credit card which I paid off every month to avoid finance charges! "Is this true, Katie?"

Katie had a look on her face like she had just been shot. "Well, yes, babe, b-b-but after we're married I was going take a second job to pay off my car and my credit card debt. And no more spending! I'm going to cut up my credit cards, I swear!"

Now I was skeptical. "How can you work two jobs, study, and go to school? You'll never sleep!" Since I began to participate, Momma had gone strangely quiet. She did surreptitiously refill Katie's wine glass, however. Katie seemed not to notice and kept drinking.

Katie's eyes were beginning to tear up. "I know people that done it," she said in a pleading tone. I noticed her grammar was slipping and she was starting to slur her words. "Please babe, I'll work my ass off and still be the besht wife in the world for you. I'll cook and clean and do laundry and all that fucking shit!" Katie took another big gulp of her wine. "I'll do ANYTHING for you, I shwear! Anything!"

An idea formed in my mind. If I was going to marry this girl, I wanted to get the measure of her resolve. Since she was well on her way to being drunk, it seemed like a good time to test the waters.

"OK, Katie, let's see if you mean that," I said. Katie smiled, and hope began to shine in her eyes. "You've played the innocent religious virgin ever since we've started dating. I want to see how good of a fuck you'll be as my wife. I want your cherry. I don't want to wait until our wedding night."

Katie's face lit up. "Ohhhh, YESH darling!" she gushed. She reached across and took my hand, kissing it - I suspect it was because she was too drunk to get on her feet at this point.

My Momma spoke like a machine gun, her fury rising. "Not so damned fast, little missy. You think that's IT? All you have to do is give up your pussy and $50,000 in debt goes AWAY? To hell with that! Let's make it a REAL challenge. You think you have what it takes, to give James everything he wants to make him happy?"

Katie drunkenly blurted out, "Oh, fuck yesh! I'll give myself to him, body and soul!" She shook her big tits at me lasciviously to emphasize her point.

Momma retorted, "Again I say 'bullshit'! He can get anything he wants here at home, and more. In fact, I challenge you to see who can make him happier for seven days."

I was stunned, not knowing what to say. I suspected my sister had warned Momma ahead of time, as it was obvious my mother had really thought this out. With the amount of wine she had been drinking, no way could this have been improvised. I was curious as hell as to what other tricks she had up her sleeve.

Katie, now confident her pussy would win out, shot back, "OK you old hag, you're on!"

Wrong thing to say to Momma. "Old hag? You little shit, I'm only 36. I got plenty of gas left in my tank. But not so fast - there's one more condition. Are you taking birth control pills?"

Another curveball from Momma. Puzzled, Katie stammered, "N-n-no, I'm really a virgin."

"Good. When did your last period start?" This seemed to be an odd question, but I felt stirrings in my crotch as to where it was going.

Katie took a second and counted on her fingers before replying. "Sunday the 14th."

All business now, Momma responded, "That works out nicely. Mine started the 13th, and today's the 28th, so both of us should be very fertile right now. Here's the extra-credit portion of the quiz, sweet cheeks. Whatever we do to make James happy, there will be no birth control pills, no condom, nothing. If you really want him, you take the risk of ending up alone and pregnant with a shitload of debt and no way to finish school if you lose. If you really want him more than anything, you'll take that risk."

Jennifer was right when she said Momma and Katie were emotionally matched - although the wine was definitely impairing her ability to think rationally I was impressed as Katie fought back and demanded, "OK, so maybe I get pregnant and all that other shit. What about you? What's YOUR risk?"

What Momma said next floored me. Narrowing her eyes, she replied in a low voice that was almost threatening. "Like I said, we're both fertile. What exactly did you think I'm going to do with him for 7 days, sew his socks, plant flowers and bake cookies? Same risk - being alone and pregnant."

The meaning of what Momma said took a bit to sink in. Katie looked to be in a drunken state of shock, while Momma sat there looking very self-satisfied. There was no doubt in my mind she had thought this out for days, and was planning on winning.

And me? I was certainly stunned, but the shock wore off as my cock started getting really hard at the implications of two beautiful hot women trying to outdo each other sexually, with me as the grand prize! Daaaaaaamn!

Momma continued, "Listen up you dumb big-titted tramp, the rules are simple enough even you should be able to understand them. We'll start tomorrow the 29th. During the week, James gets off work at 5. He'll reach either my house or your apartment by 5:30pm. There will be two shifts of six and a half hours, unless his royal highness here wants to stay longer or, in your pathetic case I'm guessing he'll want to leave after a few minutes. First shift will be 5:30pm to midnight. Second shift runs until 6:30am, which gives him an hour to get ready before he leaves for work if he can walk, although when I'm through with him it probably be difficult."

She openly leered at me and licked her lips after that last sentence. I thought my cock was already hard, but that look got it harder. "On Saturday and Sunday, first shift starts at 7:30am and second starts at 7:30pm." She stopped talking and drained the rest of her wine glass.

She took a deep breath and continued. "Which of us gets him first Monday night will be decided by a draw of the cards; every night thereafter he'll start with whichever of us pleased him more the night before. Monday morning June 5th at 6:30am, whoever has the most firsts and has pleased him the most will be the winner. So that's it. Do you understand the contest rules, or is it too much for your widdle tiny bimbo brain?"

Now in an alcohol-fueled fog, Katie was not as quick to recover her wits as she had been. The situation that was overwhelming her. On the edge of crying, she looked at me teary-eyed and begged, panic stricken, "JAMES! Please! She can't be serious! You love me! Please don't let this happen - it's not only disgusting, it's sinful! Tell her there's no way you're agreeing to this contest!" The pleading sound in her voice only made me hornier.

I leaned back in my chair and gave her my hardest stare. 'Katie, if you think Toni Barnett isn't serious, you don't know my momma. This is not the wine talking, it's her. She may have dropped out of high school, but she's one of the smartest women in town. As well as one of the sexiest."

When I said that, I saw Momma's eyes light up in delight. I couldn't tell if she was not expecting my positive response, or truly hoping for it.

"As for me not agreeing to it," I said as my eyes were narrowing, "I DO agree to it. In fact, I think it's pure genius. $50,000 is a lot of debt. So you either agree to the contest and the risks, or we're through."

I waited, thinking Katie's bluff had been called and expected her to give up and dump me. It was like in the movie "High Noon" - the only sound was the ticking of the kitchen clock. Katie's head was hung low, almost as if she was admitting defeat.

After a few seconds (that seemed like hours), she suddenly raised her head, grabbed her wine glass and drained it. Looking straight into my eyes, she spoke to my Momma; "You're on, you dried-up old twat. James is going to be all mine."

Momma slapped a deck of cards on the table between the two of them. "Pick a card."

Katie took the top card. Momma cut the deck and took one from the middle. Silently, they flipped cards over simultaneously. Momma's was the deuce of clubs. Katie's was the queen of hearts.

Katie staggered to her feet and planted a wine-soaked kiss on my forehead. "See you tomorrow at 5:30, lover", she announced, defiantly glaring at Momma. "Better take your vitamins, James. You're going to need them." At that, she staggered out the door.

To paraphrase Sherlock Holmes, "The game was afoot!"