All Bets Are Off (Pt. 01)

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My sister and her best friend have been making bets. On me.
9k words
4.78
51.4k
147

Part 1 of the 3 part series

Updated 01/14/2024
Created 01/01/2024
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**Thank you to neuroparenthetical for outstanding editing work. All errors are my own fault.**

I pulled The Mustang into the driveway --and yes, that was its name -- for once, not worrying about blocking my parents in. They were going to be up north at Aunt Kathy's place until Sunday night, so I didn't have to worry. Kathy lived in the Seattle, where they had fabled things like "culture" and "art" and "decent music clubs." Our town, however, had more farmer's markets than your average Hallmark movie, which was at least something...

Coach had called a long practice that day, and I was beat. All I really wanted in life was food and a shower, not in that order. College football, even small college ball, was a lot tougher than it was in high school. We were in a bye week, so there was no game on the next day, not that I would make the field on an average Saturday afternoon anyway. At least I made the team after a weird freshman year.

I climbed the curve of concrete stairs to the front door. It opened to a landing that had stairs leading up and down, an old split-level house. It was very 1970s, but I liked it because the place was big. Dad liked it because he got it cheap, and we all loved the pool we put in a few years later.

I started up the stairs and heard my sister, Kaleigh, downstairs. "Mom said to order a pizza," I yelled down the stairway.

"Okay, I'll order it. Natalie is staying over. We're studying for midterms."

"Fine," I yelled down, "but none of that vegetarian crap. You order it to feel good, eat half a slice, and then eat the rest of the peperoni. Just order peperoni!"

"Bite me!" she called back. But she was laughing.

My bedroom was by the basement, but we didn't have a shower down there, so I kept a small drawer of clean clothes in the small upstairs bathroom, which, according to the house rules, was where I was supposed to shower. But as usual, when my parents were out of town, I grabbed my stuff and headed to their room to shower.

My parents' shower was huge, and fantastic, like its own room, which I think it was at one time. Glass and dark tile, with two shower heads and other accouterments, it looked like it belonged in a high-end spa. Sometimes the most important thing in the world is dumping sufficient hot water over one's head, and their custom shower was built for it.

Natalie was spending the night, I thought as I started one of the shower heads. That could be interesting. Of course, it wouldn't be, but still, a thought was free and didn't get you slapped. She was Kaleigh's best friend, and they had been inseparable for ten years. And they couldn't be more different.

Two years younger than me, Kaleigh was cute, with a capital "C." She had Dad's red hair hanging past her shoulders, a sprinkling of freckles, blue eyes, pale skin, the whole Irish package. Short, slender, with an athlete's build -- she had done gymnastics for years. But gymnastics has a tendency to take over not just a gymnast's life but the whole family's as well, so she had transitioned to softball, weights, and yoga. She made the Tallmore College softball team her first year. If you were casting a cute "girl next door" type, my sister would be the one you choose.

Natalie was almost her opposite. She was a Playmate waiting for the paint to dry. A mass of dark curls down her back. Dark eyes with full lashes. And a lush body, a woman's body. Long legs, full ass, and boobs, oh her boobs. I am not a tit man. Not that I don't like them, I love them, along with every part of a woman. But unlike some guys, they are not my obsession. My obsession? Belly buttons. It was bad enough that I had to quit my job as a lifeguard at the local pool a summer ago as I couldn't stand up. But even so, Natalie's chest was a wonder. "Spathic," to use a word from my Geology class. I remembered her hanging around in our pool last year, in a one-piece that was a little too small. Remembered the way it cupped her breasts, her labia, remembered the dark pussy hair peeking out around the cloth. I imagined the way her nipples looked as she peeled out of it...

Looking down, and yep, I was hard as a rock. It has been a couple of months since I broke up with Sally, and it had been a dry period. I squirted a couple of shots of my mom's conditioner into my hand and started stroking. I closed my eyes and imagined Natalie's full lips wrapped around my cock, sucking deep into her beautiful mouth. I reached down and pulled the straps of her suit over her shoulders and down, freeing her beautiful chest. In my imagination, her nipples were large and pink, and she gasped as I pulled my cock out of her mouth and drove it between her huge tits. I leaned my head against the shower wall as I exploded, shooting cum onto her throat, splashing onto her beautiful face. I groaned as I jerked myself off. Shaking a moment, I resumed washing myself as my cock deflated, then cleaned up. And that was as close as I would ever get with her, I thought to myself with a laugh. She was so far out of my league, we might as well have been playing different sports.

In a clean pair of sweats and an old concert tee, I was coming back down when my phone let me know the delivery guy was here. Kaleigh had paid and added a tip beforehand, which meant the pizza got to us hot. We always tip well with Dad's card. I grabbed the box, thanked the driver and headed downstairs. "Pizza's here," I called.

"Great," I heard from my sister. "Grab me a beer."

I swung through the daylight basement that went out to the pool area. I pulled some cans and a box from the mini-fridge in the corner before heading into what we just called the basement, regardless that it was technically all a basement, and the original seller probably called it a "rumpus room." On our ridiculously long couch sat the two girls. In front of them was a coffee table covered in textbooks, notebooks, a pile of flash cards, and two laptops, both open. A couple of dead Monster cans lay on the floor.

Natalie hopped up to move some textbooks books over to the bar in the corner of the room, which was dry as a Utah Saturday night and covered in old junk. It had been a while since the parents had entertained down here. I thanked her and put down the pizza box along with some paper plates, napkins, and packs of pepper flakes that came with it. I have yet to know anyone who added pepper flakes, but there was always a first time.

"Beer me," said Kaleigh, still reading from a textbook. I tossed her her beverage and she caught it without looking up. She looked up at me with a pained expression. "Really. A juice box?"

I nodded sagely as I handed a laughing Natalie a can of Coke. "Really. One, you are too young. Two, you are in training. Three, you hate beer."

"Natalie is almost old enough," she said, but she still took the can of soda I offered her as well.

"'Almost nineteen' is not 'almost old enough" to drink. Hell, I'm not old enough to drink."'

"And I'm almost nineteen too," Kaleigh said in an indignant voice.

"Five months away is not 'almost' either, pixie girl." I sat down and offered the girls a slice from the box. Peperoni, and not a vegetable to be seen. "Drink your juice box."

She sat down and stuck her tongue out at me. "If we were in Canada, I would be old enough."

I laughed. "We are not driving to Canada to get you a beer, and, I repeat, you don't like beer."

She pouted as she took a pull from her Coke. "Maybe I would like Canadian beer," she said morosely, then grinned.

Kaleigh was wearing blue basketball shorts that hung to her knees in a white softball t-shirt. Her hair was pulled up in a ponytail and hung down her back. Natalie was in a pair of jeans and a dark blouse, opened up enough to show a bit of cleavage, and her mass of hair was hanging loose down over her chest and back. All told, it was a pretty normal vibe for the three of us.

I was on one end of the long couch, with Natalie at the other, and Kaleigh in a chair beside Nat. The pizza covered the coffee table. We were talking school, gossip, movies, and bets. The two of them were always betting each other, mostly about stupid stuff and grades, and they had a ledger with a running tally. Currently, Kaleigh was ahead of Natalie to the tune of $80. No actual money ever changed hands, but a dollar was sexier than a point tally, I suppose.

I asked what their plans were for the night. They exchanged glances. "Les brains are fried, from French," said my sister, and Natalie laughed. "We are taking a break before digging into Early Italian Renaissance History." Both girls made gagging noises and rolled their eyes. "Do you need to go study?" she asked.

"Nope," I said, using a napkin to pat the oil from another slice. "I've got it down." I looked at them sagely and raised my index finger. "Cramming only works if you don't know that material." I dodged used napkins. "I either know it or I don't, and cramming just shoves out stuff I know for new stuff, at least for me."

Since it was their first term, they were taking the classes very seriously, but either of them were smarter and I was. I should have been a junior, but I'd ended up taking part of my freshman year off to help Dad when his business had had a setback, and that kept me a sophomore. It had hurt football a bit, but it wasn't as if the SEC was waiting for me to transfer.

"Want to watch a movie?" Kaleigh asked.

"How about a zombie flick?" I asked. "Since, you know, brains?" I said "brains" in an exaggerated groan. The thought of Natalie ducking into my arms may have crossed my mind.

Natalie threw a pillow at me. "Goofball. No, something stupid and light." She grabbed the remote and started scrolling. I sat there and thought about how her shirt hugged her tits.

Dammit, I said to myself, you just jerked off. Settle down.

I think Kaleigh caught me looking, but she just smirked. Natalie found something, and we all sat back to watch. It was some rom-com, but more com than rom, so I didn't hate it. I glanced over at Natalie, and...

Wait, did she have another button undone on her blouse?

You, sir, are imagining things, I thought, and tried to focus on the movie.

Within a few minutes, I glanced over at her again. Now I know I was right. She had three buttons undone, and I could now see her lacy black bra on one side, a smooth expanse of skin, and the dark valley between.

Holy shit! Had I fallen asleep? Was I dreaming again? I felt my cock move, which wasn't definitive one way or the other.

I looked over at Kaleigh, but she was studiously involved with the movie. I looked back at Natalie and directly into her dark eyes. She was smiling at me, and took one of her full lips between her teeth. She reached up and slid her fingers into her bra cup, and gave the firm flesh a squeeze. Then she put her hand back to her side and turned again to the movie.

Yep, I decided, I am asleep. I am going to have a wet dream thinking about Natalie seducing me, and I will never ever live it down and have to move and become a monk. I slapped myself. Twice.

The girls were both looking at me. "Everything alright over there?" Natalie asked.

"Yeah, sorry, just thought I was falling asleep." I was definitely not asleep, and my cheek hurt.

"I'm bored too," Natalie said. I looked, for science, and yes, three buttons on her shirt were still undone. "Want to play 'truth or dare'?"

Yes! yelled the inside of my head.

"No," said Kaleigh.

"Why not?" Natalie asked.

"Because we aren't fifteen, and I don't want to end up running around the house naked or kissing my best friend. I know how these end up."

I stood up. "You figure out what you want to do, I'm going to go grab some water. Anyone want?"

They both did, and continued talking as I walked out. I ran down to my bathroom first and brushed my teeth because I wasn't a Boy Scout, but I wanted to be prepared. Then I ran to the fridge, grabbed three waters, and headed back to the basement door.

"No because it is stupid," I heard Kaleigh say. "You are an adult. Theoretically. If you want to kiss my brother, kiss my brother."

I backed up three steps from the door, but no further revelations came. After putting on a calm face, I walked back calmly, as if I hadn't heard anything.

"Here you go," I said, tossing the plastic bottles. "What's the plan?"

"No plan," said Kaleigh. "We are watching the movie."

"Works for me," I said, drinking deeply of the water. Dammit, I grumbled in my mind.

Ten minutes later, I looked over at Natalie, figuring she would either be completely nude, or dressed again. Instead, she was still partially undone, and looking directly at me again "Anyone ever told you that you're cute?" she asked.

Kaleigh snorted. "That sounded like a quote from the movie."

Natalie stuck her tongue out at her best friend. Then she stood up, walked down the couch, and sat right next to me. "Put your arm around me," she said.

The "Why?" just rolled out of my mouth, and my brain wanted to punch it.

She looked at me like I was an idiot. "Because I'm cold," she said.

I did so, more or less, putting my hand on the couch back rather than her shoulder.

She rolled her head to look at me like I was an idiot. Again. Then she put her fingers in my hair and brought her mouth to mine. I was so surprised that I didn't kiss her back at first. Her mouth was as warm and soft as I imagined, and after a few kisses, my tongue found hers. I put one hand into the soft mass of dark hair at the back of her head, and the other at her waist. We kissed for a few minutes before she broke off to turn to my sister, whom, I will fully admit, I had completely forgotten about.

"You okay with this?" Natalie asked her.

"Yeah, whatever," Kaleigh said. "It's fine." She sounded a little annoyed and bored herself as she stood up from the chair and headed out of the room. I was about to stop her, hard as it would have been, to go back to watching the movie because even with that rush of lust that was hitting me, I knew this was rude. But Natalie turned back to me with that mouth, and that was about all of that.

We kissed for several minutes while it sank in that this wasn't a "get to know you" make out session. Partly because we had known each other for ten years, but partly because Natalie leaned over and grabbed my hard cock through my sweats and started to stroke it.

I groaned against her mouth and ran my hands across her stomach. I could feel the muscles under the soft, yielding flesh, and I slid my hands under her shirt and over her bra. She grabbed my hands for a moment, stilling them, and pulled away.

"I have an idea," she said, as she unbuttoned the last few buttons and drew off the blouse. She looked astonishing in her lacy black bra and blue jeans, looking at me under heavy lids. She picked up one of my hands and placed it on her breast, squeezing my fingers around her. It was everything I had imagined, heaven in my hand. I continued to gently massage as I leaned my face forward and kissed the exposed skin around the bra cup. It was like warm silk under my lips. She tossed her head back as I ran my tongue between her breasts. I found out what angels tasted like. I heard her breath catch as I ran my tongue toward the bra cup.

She pushed back against me. "I said, 'I have an idea,'" she repeated, with a wanton smile. "Trust me?" I couldn't speak, only nod. She smiled even more. "Then trust me."

First, she pulled out a hair tie and pulled her hair back into a thick ponytail. My eyes never left her tits. She laughed at that, and took the blouse, wrapped it around my head covering my eyes and nose, but leaving my mouth free. I felt her take the arms and wrap them round my head, then tie them together. The blouse was thick, and I couldn't see a blessed thing. "Are you okay," she whispered into my ear, which was only partially covered.

"Yes," I said, and my voice cracked. She laughed into my ear and bit the lobe. I felt her lift my shirt up, and I helped her slide it over my arms. I heard a little noise of approval as I leaned back into the couch. I smiled under my blindfold. Years of hard work and sweat were suddenly worth it for that little noise alone.

She started at my throat and kissed down my chest. I felt her lips over my still thundering heart. Then I gasped as she sucked my nipple between her lips. Moving back to my ear, she laughed. "There, I got to do it first," she teased. "What, did you think I didn't notice? You have been staring at my tits for years. Did you think my swimsuit was an accident?" She started kissing down my torso again as I pondered that. "I wanted to do this last year, but you would have thought I was too young."

True, I thought, and she would have been. Graduation had changed things.

"But it didn't stop you from looking at my pretty little boobies, did it?"

"Or your ass," I added. "Your ass looked fantastic in that suit."

She laughed again, and I felt her slide from my body. Her fingers were at the waist of my sweatpants, and my boxers. "Speaking of asses, lift yours up."

I did as told, and she quickly pulled both off me, lifting my legs to pull them through. I sat there for a moment, naked except for the blindfold. I felt the cool air on my skin, and I was achingly hard. I felt her take each of my hands and slide them under my naked ass.

"Don't move them," she said. "Promise?"

I nodded, not daring to speak.

I sat, silent, and was struck with the sudden fear that she was going to yell "surprise" and take my picture and run off or something. But just as I was about to do...something, I felt her warm, soft wet lips wrap around the head of my cock. I threw my head back and groaned in ecstasy. She laughed, and I knew it because I felt the burst of air from her nose. Slowly -- so fucking slowly -- she slid her mouth down my hard shaft, then back up, then further down, taking my dick deeper and deeper into her sweet mouth. After a few moments, she had a good amount of my cock in her mouth and began to find a good rhythm of strokes.

"Oh, god," I breathed. She continued to blow me, stopping every once in a while to run her soft tongue around the head of my cock.

I wasn't a virgin -- hadn't been for a bit. I had been with several girls over my high school years and into college. My latest ex, Sally Walters, had been truly talented at sucking cock. She had, in fact, sucked several different ones while we'd dated, which was why she was my ex. But with the build up, the kink of the mask, and the fact that this was my little sister's beautiful best friend, this was undoubtedly the best blow job I had ever received. I was so glad I had jerked off in the shower, or I would have shot off immediately. As it was, I was running multiplication tables in my head to keep under control.

She pulled her mouth off with an audible pop, but kept stroking my shaft with her hand. Then she pushed my legs further apart, and I felt her mouth on my scrotum, something Sally Walters had refused to do, so fuck her. Natalie cupped my balls in her hand and licked the sack, then kissing, then licking again. Her tongue was licking up my shaft before her amazing mouth enfolded the head of my cock. Sucking tightly to the head, she ran her tongue around and around. I threw my head back against the couch again. It took all I had not to reach up and grab her head, but I promised. I whispered the first thing I could think of. "God, I want to fuck you."

She stopped, pulled her mouth off my cock. "Say it again," she whispered, so soft that I felt it against my skin as much as I heard it. "Please, say it again."

Slowly, enunciating clearly, I said, "I want to fuck you. Now. Hard. There is nothing I have ever wanted as much as fucking you."

I felt her slowly wrap her lips around me again. Then, just as slowly, she slid down until she had fit as much of me into her mouth. Then she moved her head and swallowed, and I felt the head of my cock slide into her throat. It was the most amazing thing I had ever felt. She kept going until I felt her nose against my pubic hair.