Sister Wins a Bet with Me

Everyone having sex is at least 18. This story is a work of fiction. I made it all up. Check reality at the door and enjoy it for what it is. Special thanks to goducks111 for his help and making this a better story.

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Chapter 4 -- Paid in Full

Once we hit home, mom starts making dinner. Dad starts mowing the lawn. I go up to my bedroom, and Sandy soon follows me to my room. Sometime while I was stripping down to my boxers, Sandy shows up at my doorway and watches me strip. I half expected her to strip me.

I pull back the sheet and get in bed to sleep some more. Sandy enters my room and sits on the side of my bed. She reaches over and plays with my hair again. I washed my thick, medium length hair this morning, it's light and fluffy.

Sandy is having trouble talking, "B-Bill? I want to use the last of my payments. Is that ok?"

I don't respond. I know what she wants already, she is still horny. She has needs. Trey isn't here to fill them.

"Bill, for the last payment, I want you to fuck me," Sandy mumbled.

Finally! The words I have been longing to hear. I roll to my side and then sit up on the opposite side of the bed from Sandy. I stand up and move around to her. I bend over and kiss her softly on the lips. She stands up slowly, so we never lose the kiss. Two minutes in, her mouth opens, and her tongue is stuck out as far as it goes. My tongue slides along the edges for a while. Sandy pulls away.

She makes a display of removing her t-shirt. She has no bra underneath. I latch on to her nipples and suck the nipples and part of her breast into my mouth. There, my tongue plays with the hard nubs and stimulate her breast. The opposite breast gets squeezed with a fair amount of strength. I don't want to cause pain, yet I want her to know I am busy there.

For her part, Sandy is moaning loud enough that I am worried about our parents. I really don't want them interrupting us. With the places we were taken, they must know what Sandy and I are doing. They aren't stupid people.

I lift Sandy up and place her on her back, feet towards me on the side of the bed. While her legs are up, I pull down her shorts. No panties, not surprised. That seems to be a theme today. With Sandy on her back and now naked, I drop to my knees and am at the perfect height to eat pussy.

I start with a good tongue lashing. Hard, strong, and with purpose. My tongue is hitting everything on the outside, and after I push in further, I reach the inside pink stuff. The outer lips are first, they pull up and down, right, and left. The insides get it next. Sandy has long outer lips, I made sure to push her legs further back, allowing me to get all her lips. Sandy loves this and is moaning and screaming softly at each of her small orgasms.

I haven't done anything spectacular yet. This is the warmup. When I finish with the outside, I must dig further to get the inner petals. Once there, I slow down, I am more methodical. I use far less force. I take my time and enjoy myself. Damn, she tastes good. This is a Georgia peach plucked just at the peak of its ripeness.

Now the mini orgasms are more intense. Sandy stops breathing for a few seconds and seems frozen. The orgasms are coming faster. With my tongue against her inner and outer lips and her clit, I hum a short song. That must have been a new sensation to my poor sister. Maybe it was a culmination of everything. Whatever it was, Sandy screams and goes stiff as a board. Her entire body tightens every muscle.

I get a gush of fluids in her pussy. I lap that up; I stay there until she can move. She rolls over. Did I do something wrong? I sit on the edge of the bed, wondering where I went wrong.

Sandy awakes from her orgasm and moves to the center of the bed, then says, "I'm ready."

I am still sitting on the edge of the bed, "I don't understand what I did wrong."

Sandy seems confused, "You did something wrong?"

She is mocking me, now I feel worse, "You pulled away from me, curled up into a fetal position, and then went silent after a scream. I don't understand how I hurt you."

My cruel insensitive bitch sister laughs at me, "Ohhhhh Bill. You didn't hurt me; you did the best thing ever to me." Now I am perplexed. "You gave me a bunch of small orgasms. They were good. Then you dropped a bomb on me and shattered me into a million pieces. I went to a personal space where it was just light, warmth, and joy. The joy consumed me. I came crashing back to this world, and because you didn't stop, I kept going back. A woman can only take so much."

I crawl up onto the bed. She has her legs spread wide already. I look into her eyes; this will change our relationship forever. Sandy can see the trepidation in me.

Sandy softly says, "I know this will change everything. It will be different, better, more fulfilling. I have wanted this for a long time. I need you to push forward."

Before she changes her mind, I push forward. My thick cock goes into her hole. It's an awesome feeling. She isn't used to me, I go slow. She is moaning way too loud. Does she want our parents to hear us? I wouldn't be surprised. They might be just outside of our door listening.

That spurs me on to go faster. We don't have forever, yet I don't want to go too fast, I don't have the stamina for that. I slow down. Damn! This is fucking incredible. The side of my cock feels sooooo good going in and out of my sister. She loves it, she grunts way too loud with each thrust. I push in and pull out, push in, and pull out. Over and over, I do this. I am soon drunk feeling all the joy.

I look at the clock and realize dinner will be ready soon. I need to speed this along. I pick up the pace, which makes Sandy's eyes go wide. I mouth "dinner" to her, and she understands. She stares at me as my hands hold her body in place, and I hammer my thick cock into her pussy. She is withering on the bed in ecstasy.

The grunting is now a series of way too loud moans that are building. My need is growing. Of fuck, is she on the pill?

I grunt out the words, "Cum. Where. Spray. Baby."

Somehow, she understood that code and wraps her legs around me. I won't be pulling out any time soon. I will be finishing inside of her. Sandy looks cute; she has turned pink like she is blushing. She is fighting for her breath she's moaning so hard. Her makeup is a mess, its funny right now. It looks like she has black tears. We are both sweating hard, it's hard to hold her in place.

Oh, shit, "San-dy, al-most, there!"

It wasn't more than three more strokes; I lost control. I shoot my cum deep into my sister. It's incredible at how much joy each shot of cum brings to a man. It's fulfilling to see the pleasure in your partner's face. It's incredible having the joy shoot through your body, and the physical act brings a terrific feeling to me as well. Then the world ended.

Sandy bellows the loudest scream of her life. Not only did the parents hear that, but the neighbors as well. What's worse, every muscle, including the legs around me, have constricted. I am locked in this position, unable to move, and I hear someone running up the stairs. I try to push Sandy, she isn't moving. Oh Shit! She isn't breathing!

I scream out, "Help!"

In moments, mom busts into my room. First is the "Oh shit, what the fuck are you doing?" Then "Oh shit, my daughter isn't breathing." She rushes to Sandy and holds her head in her hands, she is loud when she calls her name. Nothing. Mom slaps her on the back a few times. Nothing. Now, mom is almost freaking out when Sandy's eye spring wide open and she starts breathing hard for a breath like she was holding it too long.

Sandy is excited as she loosens her hold around me and shouts, "Damn Bill, that was fantastic for your first time. Oh fuck, mom, what are you doing here?"

It doesn't take a genius to figure out she is pissed. Mom is rather cool considering what she can see we did.

Mom walks to the door and says, "Dinner in fifteen minutes. I want you two showered. GO!"

We both sprint to the shower and start up the hot and cold as she likes it. While it's getting hot enough, I turn Sandy around and kiss her with an intense kiss.

I then say with a macho voice, "That was awesome. As long as you don't have a boyfriend, I don't mind assisting all you want. YOU were amazing."

Chapter 5 -- Dinner Conversation

We both go down to dinner, dreading the consequences and the punishment. Dad is sitting at the end of the six-person table. Sandy and I sit next to each other, the opposite side is against a wall. Mom will sit facing dad when she finishes cooking.

Dad says in his normal voice, "Gail...."

Mom looks at dad with a pleading look, he is emotionless. Mom looks at the floor. Mom's shoulders slump, and then she takes off her t-shirt. She isn't wearing a bra; she knew this was coming. She pulls down her shorts, not even a thong. She does have an apron there, she put that on now. Mom has large breasts, and the apron doesn't hide much.

When mom serves the food, she takes off the apron. Dad did help by setting the table, don't think mom does everything.

Sandy doesn't quite know what to ask, she tries, "Mom ... what ... why ...how?"

Mom smiles, "I lost a bet with your father. I'll be naked all week unless I need to go in a car. Inside, outside, answer the door, all naked. The second bet..."

Dad is surprised, "The second bet?"

Mom does a heavy sigh and says, "I bet Bill that he couldn't force his sister to fuck him. At stake was three months as a personal sex slave when you're not using me."

Sandy shoots up, standing, and yells down at me, "You mother fucker, you did all of that just to get me to fuck you? You piece of shit! I thought I messed you up! You're the one that's fucked up."

I am defensive, "Hey, it wasn't entirely my fault. I set you up for six months by forcing you to do mundane punishments, then, when you win, you make me blow your boyfriend? What the fucks with that? I obviously didn't intend on that happening nor that you cheated on Trey with Tony. So no, my entire plan went to hell. I had to improvise."

Dad continues, "He told me about his plan and how he was going to get there. I now owe him an apartment at college when he goes. Your mom was getting bored with the dogging, nudist camp and the glory hole. I figured with Bill being young, he'd have more exotic ideas for his mom. She gets the sex she needs, and I don't worry about him taking his mother."

Sandy asks a good question, "Why is mom safe with Bill?"

Mom answers with a scowl, "Because he is fucking you as well."

Mom is thinking. Oh shit. Technically, she had to hear Sandy ask me. Dad saves me.

Dad is amused as he says to mom, "Zip it, honey. Don't you think losing will be more fun than winning this time? Think about it." Mom smiles at me. Awesome.

Sandy is confused, "Did I lose?"

Mom laughs at her daughter, "No, my dear, you didn't lose. You come out of this well. You can go and get a boyfriend, or Bill will take care of your needs. You have a choice. I, on the other hand, will be ravaged by my husband and a young man with way too many uncontrollable hormones. Said boy can now force me to do almost anything in the house and in public.

"I will be at his beck and call doing anything that a young man can think of. The one detail he must abide by, while not at college, he must fuck me at least once a day. Your father added that detail to help quell my sex drive, I assume."

I fill in for Sandy, "I'm going to the local community college for two years. Then dad will pay for an apartment for my last two years of college. He'll let me have a two-bedroom apartment if you want to share with me your senior year. Maybe you'll have a boyfriend, so we won't force you."

Sandy asks me, "Will you start using condoms?"

I smile back at her, "No." She looks disappointed. "As long as I'm with you, nobody else will be with me ... other than mom," I quickly add. "I know you have needs. I expect that I'm not your dream guy. So, I expect you will date guys still. I'll be here when you need me."

Sandy holds me, squeezes her breasts into me, and cries as she softly says, "I had boyfriends because I couldn't have you. I don't need them anymore, you silly boy."

She kisses me on the lips again, a lot longer than usual, and then sat and held me for a while to make sure I am ok. I am.

We stay and watch some Netflix for an hour with the parents. Mom and dad get up and give us the remote for the TV, they are going to bed early. Sandy turns off the TV. I turn off all the lights, and we both go upstairs. Sandy guides me to her bedroom.

She whispers in my ear, "Your sheets will be wet still. Mine are dry. I am a bit tender from earlier, is it ok to ask you ..."

I put my finger to her lips which stops her talking. I use the same finger to push her down on the bed. She raises her legs; I remove her shorts. Predictably, no panties. She may not want to fuck, but I have yet to hear a woman turn down oral.

As she lays on her back, her legs come up at the same time. I deftly remove the shorts. Still, no panties. I bend down, and Sandy rests her legs over my shoulders with my head in between those long sexy legs. The beads of liquid are flowing down; now they're flowing up. So cool.

I am gentle and relaxed in my licking. My licking starts at the clit, so it gets a workout, and then goes as far down as my tongue can reach. I don't want to be moving my head. I travel only as far as my tongue goes. Meanwhile, further down in her pussy, near the taint, I have some fingers working their way around. I want them as deep as possible while my tongue is busy.

Between my fingers rooting around and my tongue licking all that it can, Sandy blows up. This is a hard orgasm that is kicking her ass. I am disappointed, I didn't expect her to go off that quickly. I spin her body around, so her head is on a pillow. We both fall asleep.

Chapter 6 -- Monday

I wake up, no class for me today, summer has started. Mom should be making dad's breakfast. I go down to check up on her. She is making enough breakfast for her and dad. On seeing me, she adds two more strips of bacon. Mom is standing with an apron on her and nothing else. I push mom towards the table.

She puts one foot up on a chair and leans forward with her hands on the table. With her leg up, I have better access to her sex. I check the bacon, flip it, and then slide my cock into my mother. She giggles as I slowly thrust it up into my mother's dirty cunt.

Mom is flush from embarrassment, "Ohhhhhhh, that feels so good. I love the way it slides into me. I can feel everything. We don't have time, make this quick. Fuck me fast and hard if needed. That's right, oh, so goooooood."

I move to my fastest rate of fucking, and it stops the talking. Mom is a grunter. With each thrust, she lets out a loud grunt. I love the look of her long thin legs, her toned arms, and the long thin neck. She is a MILF, alright. Here I am slamming my meat into my MILF mother. That is a big mistake. Thinking those thoughts made me orgasm, leaving mom with a crappy fucking.

I am sad as I pump my cum into my mother, "Sorry, mom. I was thinking about how cool it is to be screwing my MILF mother. You deserve better than that. Next time, I will be better."

Mom is happy as she turns around. She is way too happy, work should be interesting. She tries to say something and trips over her tongue. In the end, she giggles and runs upstairs. I take her eggs and bacon for me, and I start some bacon for mom. I will wait a bit before starting the eggs. I turn down the heat. When the shower stops, I am finishing my breakfast. I put my plate and silverware in the dishwasher, drop some toast in the toaster, and then turn up the heat a bit on the frying pan.

Both mom and dad come down, looking refreshed and happy. They both eat quickly, and dad is off to work. As a reward, mom gets to suck my cock. She is thrilled to be eating cock. I like eating pussy but not nearly as much as mom loves cum. I don't complain though. This is damn good.

After breakfast, I tell mom, "Get dressed for the gym, we're going out today."

Twenty minutes later, and mom is ready to go. She drives me over to the gym so we can both do our workout routines. I'm not some huge bodybuilder guy. I have a simple routine for my arms, legs, and core that I do three times a week. Usually, I go in the evening. Right now, almost nobody is around, just a few college coeds. I change in the locker room and find mom out on a treadmill. Nobody is near her.

As I walk by, I smirk and tell her, "Lose the top and bra."

Yikes, the look she gave me could kill. There are only two people around, and none are close. Mom only has a top on, no bra, it only took a second to remove it. I continue to the weights where I start my routine. It's distracting watching mom out of the corner of my eye with her breasts moving so much.

It got real interesting when a second woman takes the treadmill right next to mom. They have like thirty of these, why the one next to mom? Holy fucking shit. The second lady, who is less endowed, took her shirt and bra off. The two of them are side by side, jogging topless. I can see them looking at me from time to time.

Sure enough, a third lady stops next to mom, and she strips 100% naked. Soon, all three are naked. It isn't long before I see mom calling me over, using hand signals. Oh crap. I walk over to the three beautiful women.

Mom says with a teasing smile, "My two gorgeous friends think you should join us. Why don't you take the treadmill in front of us? We want to watch your ass."

How stupid do they think I am? There is no way my shorts stay on longer than a minute.

I happily get on the treadmill and get a nice pace going. As soon as I hear a treadmill shut off, I slow down. I don't want them killing me. Sure enough, a hand goes to each side of my shorts and pulls them down. I suspend myself on the sidearm rails so that I am hanging in the air, while my pants are pulled down.

No laughing or giggling, they all stare at me. My feet go down, and I pick up the speed. One by one, they walk around the front to see my cock bouncing. OH MY GOD, that is a THRILL! Knowing that two strangers are looking at me is weird, knowing more could come in is just crazy. The two college girls are now next to me. I love their bouncing tits.

I tell mom, "Gail, I think these two would like their pussies cleaned. Can you do that, please?" I didn't want to call her mom in front of the girls.

Mom gave me a cheerful look and then from the front of the treadmill, put her knees on the sides, her hands on the side railings, and then leaned forward to lick a pussy. The girl slowed down to improve the oral they wanted. The angles don't work. Mom can't eat pussy from in front.

The coed stops walking and falls off the end. She is thinking about how they can make this work. Mom has already figured it out, she starts eating her where she stands. That works. The other one stops, and I get her. I want to race mom. Normal instincts tell you, go fast, I am doing the opposite.

I am slow and deliberate. My eyes are always looking up at her. I alternate sucking hard and soft while licking up and down. I rub my cheeks with my stubble along her thighs and over her slit. She screams as she orgasms and catches the rails as her legs give out.

I stand and watch mom service the other girl. The one I serviced crawls to me and sucks me into her mouth. Oh my, she must not know I am in high school. I am not about to tell her. Mom finally gets her girl off. Mom stands up, and the girl timidly moves to mom.

I stop the girl, "Hey! Don't feel that you need to service her. She loves sex and can't get enough. She had fun getting you off. Please don't feel that you must return the favor. Without wanting it, you'd be terrible anyway."