The Wager

All characters are at least eighteen years old.

*

It was the first day after high school graduation, and Michael Kellogg was going to enjoy the next five days of leisure. The following Monday afternoon he would have to start his new job at the local cheese processing plant. His parents, who are day shift supervisors, arranged for him to be hired once he graduated.

Michael had wanted to go to college, but he couldn't keep his grades high enough. It wasn't that he was unintelligent. The young man just hated studying. So, he was stuck doing manual labor until something better came along.

At 6'2", and a hundred ninety five pounds, Michael is a good looking young man. He has wavy brown hair, and a strong jaw line that has always attracted girls.

Gloria, his girlfriend is so smitten by Michael, that after they turned eighteen, she started letting him have semi-protected sex with her on a regular basis. She would rather that he use condoms, but his extra large cock sometimes caused the condoms to tear during sex. So, she would take her chances, and hopes that the birth control cream keeps her safe from pregnancy. She also makes Michael pull out before he can fill her pussy with his cum.

His over sized cock also caused problems when they first started having sex.

When Gloria first saw the monster, she wanted to back out.

However, Michael got his girlfriend to agree to try by allowing her to be on top so that she could control the pace of their love making.

It was a slow process at first.

Gloria had to rub her boyfriend's cock head across the entrance of her cunt for nearly ten minutes before she finally got the courage to lower her pussy onto the monster.

When the thick head finally did penetrate her tight hole, the girl felt like a sausage was being stuffed inside her. The twinge of pain from her hymen tearing caused her to whimper.

Gloria was determined though. She loved Michael, and wasn't going to let something like his size stop her from giving him what he wanted.

It took quite some time, but once Michael's cock had completely filled Gloria's stretched pussy, she gazed at her lover with a look of pride.

"We did it," she beamed. "I got all of you inside me."

They went slow the first few times they made love.

The third time they had sex, Michael exploded into his girlfriend's body.

Gloria wasn't sure, but something didn't feel right. She eased Michael's dick out of her cunt, only to discover that the pre-lubricated condom had broken.

She freaked out, believing that he'd just impregnated her. Fortunately, her fears were alleviated when she started her period the following week. After that she started using birth control cream as well as making Michael wear pre-lubricated condoms.

When another condom broke a few weeks later, Gloria decided she didn't want to end up with small pieces of latex inside her, so she started letting Michael fuck her bareback, with only the birth control cream for protection. She would make him pull out before ejaculating.

Libby, at nineteen, is a year older than her Brother. She is a well endowed young woman, who gets lots of attention from the local men. Her face is a little wide, yet for some reason that odd feature makes her even more attractive. Libby has shoulder length brown hair, and an infectious smile. She is a bit of a daredevil. One of her favorite hobbies is gambling. Libby will make a bet on just about anything.

Libby also works at the cheese processing plant. She works the second shift; the shift Michael would soon be working, while her parents work the first shift.

As Michael began to wake up, he kicked off the covers, and stretched. Michael had slept in the nude for as long as he could remember. His usual morning erection was standing almost straight up. As the cobwebs began to clear out of his head, the young man reached down and absently stroked his massive cock, like he usually did.

Libby, who had gotten home sometime after midnight the night before, was also waking up. She was wearing a wife beater T shirt, and a pair of cotton panties. As she sat up, and rubbed the sleep out of her eyes, she remembered that the second shift supervisor had told her to have Michael come in to fill out his safety forms.

"Just have your Brother follow you to work," Libby's supervisor had told her. "You can show him to my office before starting your shift."

Libby stretched, and stood up. "I guess I'd better let Michael know what's going on, before he takes off for the day." She didn't bother to dress, since Michael had seen her in her sleeping clothes numerous times. She left her room, and crossed the hall to her younger Brother's door. Still half asleep, she opened the door without thinking to knock.

Michael was still lying on his bed, stroking his morning erection when his older Sister walked in.

"Mike, the second shift supervisor wants..." Libby stopped dead in her tracks. All remnants of sleep instantly disappeared. "What the fuck?"

"Don't you know how to knock?" Michael exclaimed.

"I'm sorry, I just wanted to tell you that Nick wants you to come in this afternoon to fill out some forms and go over safety protocols with him." Libby couldn't take her eyes off her younger Brother's cock.

Michael couldn't help but notice that his Sister was staring. "Haven't you ever seen an erect cock before?"

She shook her head. "Not a cock that big I haven't. That thing is huge."

Michael shrugged, as he continued stroking his dick. "Yeah, I know, my dick is kind of big."

"Kind of big, are you kidding me? You put a horse to shame." Libby tried to tear her eyes away but she couldn't stop staring at her Brother's massive cock. How the hell do you get that thing inside Gloria?" She asked.

Michael squeezed his monster. "I just take my time. The first few times, I had to go slow with her. But after a while, her pussy stretched enough so that it slides in a little easier each time we fuck. Now, she can take it easily."

Libby stared at the monster. "That thing fits inside her pussy?"

"Yeah, we fuck once or twice a week. We started fucking a few months ago, after we both turned eighteen."

Libby shook her head in disbelief. "Gloria has got to be walking bowlegged by now."

"Nah, a lot of girls can take something this size."

Libby snorted. "You're dreaming little Brother. That thing would split most women's pussies wide open. The head is bigger than my fist. Your dick as got to be at least a foot long."

"A newborn baby is bigger around than my cock, and yet women deliver babies all the time."

"Yes, but they endure hours of agony delivering those babies. I can't see you waiting that long. You probably want to shove it in as quickly as you can."

Michael chuckled. "I've had to learn to be patient. I let Gloria get on top when we first started having sex. She would slowly lower herself onto my cock, taking it in as her pussy adjusted to its size. Once she got adjusted to having my cock in her, I'd roll her over on her back and fuck her missionary style. She has the best orgasms when we fuck." As Michael explained how he fucked his girlfriend, he noticed that his older Sister never took her eyes off his dick. The desire to fuck his older Sister once again roared to life. Michael had wanted to fuck Libby for as long as he could remember. As he looked his scantily clad Sister over a devious thought ran through his mind. "I'll bet if you went slowly at first, you could take a cock this big inside your pussy."

"Oh hell no," Libby shot back. "If I tried to ride a dick that big it would rip me open. Something that thick would never go inside me in the first place."

Knowing Libby's love of gambling, plus her desire to rent a place of her own, Michael made his move. "I'll bet you a hundred bucks that you could take one that big."

"You want to bet me a hundred bucks?" Her gambling bug instantly kicked in. Libby saw a great opportunity to win an easy bet. "Wait a minute, where are we going to find a dick that big to make the bet with?" Libby asked.

Michael smiled at his Sister. "In order to know that you actually tried, I'd have to witness the attempt. So, I guess we'd have to use my dick for the wager."

Libby's gaze left her Brother's dick for the first time. She stared at Michael in disbelief. "There is no way in hell I'm letting you fuck me. That would be a little too weird."

"I didn't say I was going to fuck you Sis. I just said I'd let you try to get my cock in you for the bet. Once you tried, and succeeded, or failed, we'd stop, and one of us would pay up."

Libby was torn between the strangeness of doing this and her desire to win a bet. "I don't know. I wouldn't want something that big inside me. Besides, you don't have a hundred dollars. How do you intend to pay up when you lose?"

"Simple, I'll double the bet if I lose. If you can't get my cock inside you after fifteen minutes, I will pay you two hundred dollars after I get my first paycheck."

"I don't think it would be a good idea for us to be trying this. The idea of having my Brother's dick head at the entrance to my pussy is disgusting."

"You've done more disgusting things than this to win a bet. Remember the time you swallowed six night crawlers to win three hundred dollars?"

Libby knew Michael was right. She had done some pretty bizarre things in the name of gambling. Once she streaked around the outside of her house in the middle of the afternoon to win fifty bucks from her younger Brother.

Fortunately her Parents were at work, and no one saw her but Michael.

Her gaze returned to her Brother's erection. She knew that all she'd have to do is make a half hearted attempt for fifteen minutes, and she'd win the bet. With the extra two hundred dollars, she could finally afford the deposit on an apartment, and then she could move out. "Ok, it's a bet. I try for fifteen minutes to get that thing inside. When I win, you pay me two hundred dollars after you get your first paycheck." Deciding to make the bet more difficult for Michael to win, she added, "However, your cock has to go all the way in until it reaches my cervix."

"In that case, you have to try for twenty minutes."

Libby let out a small laugh. "Sure, why not?" Libby knew that if that thing wasn't going to penetrate her in fifteen minuets, an extra five minutes wouldn't make a bit of difference. "It's a bet. However, you can't tell anyone about this."

"I won't say a word, I promise." Michael knew his Sister would only try hard enough to make it look good, but the young man had a plan. He opened the drawer to his nightstand, and pulled out a tube of KY jelly.

"What's that for?" Libby asked suspiciously.

"If you're going to be rubbing your pussy lips on my cock head for twenty minutes, I want some lubrication. I don't want you rubbing me raw."

"Just use a condom."

Michael shook his head. "That would add extra thickness to my cock. It would give you an unfair advantage. Besides, I haven't found any condoms that fit properly. They occasionally break when Gloria and I are having sex. Gloria is afraid of having pieces of condom left in her, so I always pull out before cumming when I fuck her. Plus she uses birth control cream to diminish the chances of pregnancy."

"I can't use birth control cream. It makes me itch. And there is no way you're putting your bare dick against the entrance to my pussy. If you came with your cock head shoved against the entrance, your sperm would shoot inside me, and I could end up pregnant. There's no way in hell I'm letting anyone, especially my little Brother knock me up."

Michael stared at his Sister in surprise. "Aren't you on the pill?"

"I keep meaning to get a prescription, but doctors cost money. Besides, I usually make guys wear condoms."

"Hell, you have nothing to worry about anyway. I'm not going to cum in you. I have very good self control. With a dick is as big as mine, I had to learn self control. Otherwise I'd have ejaculated long before I got my cock inside Gloria. Besides, we're not going to have sex. We're just having a friendly wager."

Libby thought about the statement for a few moments. "Yeah, I guess you would have to learn to wait before cumming. And like you said, we're not going to fuck. So, how do we do this?"

"I'll lie on my back, and you straddle me. I'll hold onto your hips, to help you keep your balance, and you ease the head of my dick against the entrance to your pussy. You then let a little weight down so that the head presses against the entrance to your cunt. You then rock back and forth a little to keep your pussy moist. As your pussy walls open up, you ease down a little farter until my cock completely fills you. Once the tip of my cock touches your cervix, you take my cock out, and I win the bet."

"Or, the thing never goes in, and I win the bet," Libby replied. Feeling excited about the two hundred dollars she was about to win, Libby stripped off her panties.

Michael opened the KY jelly and rubbed a liberal amount on his dick head, and along his shaft.

Libby approached the bed, and waited for her Brother to finish lubing up. She smiled inwardly, knowing that soon she would win two hundred dollars and have a place of her own.

Michael replaced the cap, placed the lube back on his nightstand, and then laid back. "Ok, climb on."

Libby climbed onto the bed, and then straddled her Brother. She grasped his shaft and lined it up with the entrance to her cunt. She felt strange holding her Brother's cock head against the entrance to her cunt, but a bet is a bet; and Libby intended to win.

His dick was so long that she didn't have to lower her hips very far for it to touch the entrance to her pussy.

"Get ready to lose two hundred dollars, little Brother. There is no way this thing will ever get past the entrance, much less go completely inside me."

Michael didn't say a word. He knew from experience with Gloria that Libby's pussy would stretch to accommodate the thickness of his cock. The head of his cock would be in his Sister before she even realized what had happened. Once he got past the entrance, there would be no stopping him. He'd fuck his Sister until she screamed.

Grasping Libby's hips, he gave her a small nod. "Check the clock to see when we begin."

Libby checked the clock on the nightstand. "It's nine thirty five. At nine fifty five we stop." She began rubbing her Brother's cock head back and forth across the entrance to her cunt. As she rubbed his manhood through her vaginal lips, and across her fuck hole, Michael applied gentle pressure to her hips.

"Don't try forcing me down," Libby warned. "If you force that thing in me, it'll be cheating. Plus you'll hurt me."

"I'm not going to force my dick into you. I just want to make sure you don't cheat. If my cock starts going in, you have to let it. You can't hold back, or you forfeit the bet, and pay up."

Libby kept rubbing the head of her Brother's dick across her entrance. With each pass she'd rub the tip against her clit.

Michael held firmly to his Sister's hips, making sure she kept enough pressure to cause penetration once her vagina opened up enough to accept his cock head.

After several minutes of rubbing Michael's cock head across her clit, Libby's body began to respond to the stimulation. Her clit became inflamed, and her vaginal opening began to expand. Her pussy was getting ready to be fucked.

Libby glanced at the clock. A smile appeared on her face.

Seven minutes had passed, and he hadn't penetrated her yet.

"I am so looking forward to winning this bet." She continued to rub his tip along her slit.

Michael felt the tip of his cock penetrating the entrance to his Sister's pussy as she rubbed it through the fold of her labia. He smiled inwardly knowing her cunt was ready for penetration. "Ok sis, you need to stop rubbing, and rest some of your weight onto my cock to see if it will go inside."

Libby swallowed hard. She didn't believe the thing would go inside, but she was still a little nervous. Taking a breath, she allowed some of her weight to rest on her Brother's cock head.

Part of Michael's cock head slid inside his Sister's pussy.

Libby gasped involuntarily. Her body shuddered, as the monster spread the entrance to her cunt open. She tried to rise back up, but her Brother held her in place.

"Hold still," Michael instructed his Sister. "Let your pussy get used to being penetrated."

For the first time, the pretty nineteen year old began to suspect that she might lose the bet. "Fuck," she seethed under her breath. Libby was sure that because it was her Brother trying to penetrate her pussy, she would stay dry enough to prevent him from entering her cunt.

However, between the KY jelly, and the stimulation of her clit; her pussy did what came naturally, and opened up. Her body didn't care who was trying to fuck her. Her cunt was doing what it was designed to do.

Libby felt the monstrous head spreading her open. She shuddered again as pussy walls spread further.

"Let your body lower a little more," Michael said.

Libby closed her eyes, and gritted her teeth. She didn't want to follow her Brother's instructions, but she had agreed to the bet. Libby let her knees bend a little more so that she would sink lower.

The rest of Michael's cock head slid into his Sister's cunt.

Libby felt her vaginal walls stretch as her Brother's cock head sank deeper into her body. She wasn't in pain, but she could definitely feel her vaginal walls stretching. "Maybe we should call this bet off," Libby said weakly. She knew her Brother would never agree to it, but she had to try.

Michael shook his head. "A bet is a bet. You're not trying to welsh on a bet are you?"

Libby gave her Brother a glare of disdain. "Your cock hasn't reached my cervix yet, little Brother. This bet is far from over."

Michael gripped his Sister's hips tightly. He slowly began lifting her up off his cock until only the tip was inside her.

Libby thought that perhaps Michael was letting her off the hook.

He then lowered her hips back down, causing her pussy to open up more.

Libby whimpered as another inch of his thick monster sank into her body. She shuddered as her Brother's cock stretched her inner walls. Libby knew she was going to lose the bet.

Now that Michael's cock head was inside her, it wouldn't take him long to sink all the way into her cunt.

"Fuck, it's too big," she pleaded, hoping he'd have mercy on her and quit. "Michael, you'll rip me apart."

"Don't worry Sis, I'll go slowly. Your pussy will stretch. And I won't force it in. We'll go only as fast as your body can handle." He gave his older Sister a devilish smile. "Look at it this way. At least you'll get the satisfaction of knowing you can take a big cock inside you."

"Yeah, but it's your big cock that's in me. This is incest."

"Nope, it's a bet. I told you I wouldn't fuck you, and I meant it. Once my cock touches your cervix, we can stop."

Libby desperately hoped that her Brother's cock wouldn't go all the way to her cervix, but deep down she knew better. She was about to lose one hundred bucks to her younger Brother. She was also about to have her younger Brother's huge cock buried in her stretched out pussy. "You promise we'll stop as soon as your dick is all the way inside me."

"I told you this is just a bet. I'm not going to fuck you." Michael was lying, but he knew that once his cock was all the way inside her pussy, Libby wouldn't want to take it out. Having her pussy stuffed to the limit would drive her into a heightened state of sexual arousal.

Her Brother's words encouraged Libby to get it over with. "I still have a chance of winning. Getting that thing in the entrance is one thing. But taking it all the way inside me is entirely different." Libby knew her only hope was to cheat. She'd pretend to try, but not let it go any deeper.