Dating My Sister

Dating my Sister

It didn't start out intentional, hell it didn't even start out as sexual; but then it never does. I was in my senior year of high school and I needed a date for prom. No I'm not a nerd, or fat and ugly. While I get decent grades, I also play soccer and basketball; I guess that makes me your normal average guy; except for one thing; I'm not wild about girls. No I'm not gay; not that I have anything against guys who are; I am just not into girls...at least ones my own age.

I'm not into the drama and the giggling; I'm not into the hair and the shoes; and God help me I HATE the gossip; which basically takes ninety percent of the girls my age out of the picture. I like porn, let's be honest I jerk off practically every day. And while there are some really hot girls in my class, I've tried dating and with all the giggling and fawning sometimes it make me want to puke.

I hadn't even planned on going to prom; but the "this isn't an option Dawson" from my dad cut that idea off. He still thinks I'm gay and I can't convince him otherwise; which meant I had to find a date or he was going to flip out.

It was Saturday morning and I was in the driveway shooting hoops with Raylene my sister; when it hit me like a load of bricks. Oh my God, Raylene is a girl. Now, you have to understand my sister is a bit different; which is why we've always gotten along great. She got to college on a basketball scholarship and she ran track in high school. She's fit, trim; and will beat the shit out of a guy in a heartbeat.

"What's with the shit eating grin?" Raylene looked at me.

"You're a girl" I said dumbly.

"No shit Dawson, what gave you the first clue; the tits?" Raylene barked out a laugh.

"No, I mean you're a GIRL" I smiled.

"Whoa, whoa, whoa" Raylene held up her hands. "You can skip that idea" she gave a scowl.

First of all Raylene knew about my rounds with Dad over the prom, hell she had heard them enough around the house. Second, my sister is both very smart, and not bad looking.

At twenty Raylene has that natural look that honestly a lot of women would kill for. She stands five nine and weighs in at maybe a hundred and twenty pounds. She's got that lithe athletes body with toned legs and muscular arms; that taut belly and a natural tan from spending years outside. Add to it a not so bad set of 34C's she keeps bound up in sports bras; even for a sister she's kind of cute.

"Come on, I'll throw in fifty bucks" I said quickly.

"First...fifty isn't near enough to date my sicko brother" she snatched the basketball from my hands. "Second, we live in the same house; I can see dad's face when I march down the stairs as your fucking date" she snorted.

"What if I make it a hundred" I added back quickly. "And I actually have an idea about how to get around the house thing" I told her.

"Look Ray" I said quickly before she could open her mouth. "You know what this about...you've been there" I threw in my biggest shot.

Raylene did know; two years ago when she was a senior she had gone through the same thing with dad. I was about the only one who knew that her prom "date" was actually a member of her basketball team she had paid a hundred dollars to fake being her date. She had pulled the same thing I was suggesting.

"Bite it" she growled. "Look Dawson he won't buy it, he'll know it was me." She sighed.

"I figure you spend how many nights over at Mel's" I shot back.

Melanie was Raylene's long time friend; and I actually suspected she might be a lover for Ray; but it was none of my business. I just knew that at least once a month Raylene spent an overnight at her friends.

"Let me get this straight, you want me to go spend the night at Mel's; and be your prom date?" She stared at me.

"It could work" I insisted. "We go to the prom, word gets back to dad I actually had a girl for a date, and he gets off my back" I argued.

"While I admit I pulled it off" Raylene shook her head. "It won't work for you" she said.

"Why not, you said it worked for you" I was desperate.

"Because girls get asked out all the time by guys." She tossed me the ball. "Guys date first Dawson; they don't just show up with a random girl." She pointed out.

"Fuck" I tried to think of an answer.

While I generally disagreed with her; in a lot of ways she was right. Dad would want to know who the girl was, how I had found her. He might not buy I was actually dating if I just went to the prom and then didn't date again.

"How about..." I was thinking fast. "I take you out for pizza, then we go for a movie; and then prom." I suggested.

Raylene looked at me for a moment, and then slowly walked up closer. She stood almost nose to nose with me; so close I could smell her sweat.

"You do know you're asking your sister out on a date" she stared at me with fire in her eyes.

"No" I said calmly. "I'm asking my best friend out on a date" I said.

The fire in her eyes dimmed and she stared at me. "Dawson..." she said slowly, and then sighed.

"I'll need to talk to Mel, if I'm staying there she is in on this; got it" she said quietly.

"Understood" I said quickly as I realized she was agreeing. "Just tell her she gets a couple extra carpet classes" I said smartly.

A bit too smartly as Raylene's slender hand came straight up and wrapped around my throat. The fire flared in her eyes as she looked at me.

"You ever say that again, I'll rip your nuts off" she hissed. "Besides" she smirked as she let go of my throat. "She tastes fucking awesome."

I just shuddered at her remark as she dropped the ball on the driveway and headed for the house. Halfway across the lawn she turned at looked at me.

"We do this the right way Dawson" she told me. "You ask proper, I'll decide; and YOU pay got it."

I just nodded happily. Once again problem solved, I figured. As I picked up the discarded basketball I wanted to hop around the driveway with joy, I had solved my prom problem. What I didn't know was I was about to create an even bigger problem I had no idea how to get out of.

A week later, after checking my finances from my part-time job; I knocked softly on Raylene's bedroom door.

"Come in" I heard from the other side.

I stepped in and looked around. I was actually shocked when for the first time I saw her room with fresh eyes. There was teddy bear sitting on her properly made bed; the smell of perfume in the room; and just a hint of pink that showed a hidden female lived here.

"Hey" I asked softly.

"Yeah" Raylene looked up from her text book she was studying from.

"I was wondering..." shuffled my feet. "Uhhh, if you are free Saturday...maybe we could go grab a pizza at Delmonico's" I looked up at her.

Raylene sat on her bed and looked at me for a moment. "I'd like that" she said softly.

"Cool" I started to turn and leave. "How is say six?" I asked quickly.

"I can't at six" Raylene shook her head. For some strange reason I felt my heart sink at her words. "How about eight?" she said back.

God help me I actually felt a surge of happiness at her sudden agreement.

"Eight works great" I said quickly. "I'll pick you up then." I told her.

I can't explain why, but I was actually thrilled I was having a date; and having it with Raylene for some reason made it even better. It wasn't some girl I had to pretend with; she knew who I was. For once I could be myself. But, I thought I was thrilled, Dad was on cloud nine. He actually spent time going through date etiquette with me; and when he was done handed me a condom. I wanted to groan with frustration.

The day before our date, I actually went out and got a haircut. For some reason it was important to me to be presentable. I showered that evening, and carefully picked out a pair of jeans and a button shirt.

I pulled up in front of Mel's place at ten before eight. I was nervous as hell; I'd never been on a real date; and my hand shook as I rang the bell.

"Hey Dawson" Mel smiled when she opened the door. "Come on in." I stepped inside the doorway and waited.

"Raylene your date is here" Mel called out. "Remember this is my girl you're taking out" she turned and looked at me. "Hands to yourself big boy" she smiled.

"Uhhh, I promise" I said softly.

"Relax Dawson" she smiled. "You look pretty good dude"

I opened my mouth to thank her; when footsteps came from the hall, and then Raylene rounded the corner. I froze in my movement and could only stare at her. I mean I knew she was a female; shit she was my sister; but holy shit. Long dark hair flowed out around her shoulders, highlighting her face and those big brown eyes. She seemed to move with a fluid grace as she walked towards us. She was wearing an angora sweater that hugged her body; those 34C's jutting straight out at me. She had on a pair of form fitting jeans that hugged her hips and muscular thighs like a second skin.

"Jesus" I whispered.

"Pretty nice package eh" Melanie chuckled at my soft outburst.

"No shit" I whispered softly as I stared at Raylene.

"You can put your tongue back in" Raylene looked at me as she picked up her purse.

I shook myself, trying to regain control. I opened the front door and held it for her.

"Have her back by eleven" Mel called out as we walked down the driveway.

I own a fairly beat up ten year old Ford truck. Most people hate trucks; that night I found another reason to love mine. I held open the passenger door and helped Raylene climb into the passenger seat. The view of that tight ass encased in those jeans; sent a surge south of the belt line like I had never felt before.

Down boy, I screamed silently to myself as I rounded the truck and climbed in. The drive to Delmonico's was quiet; but when we started to both laugh at dad giving me the condom; things finally started to open up. I have to admit; for someone who didn't date; the next two and a half hours were some of the best I could ever recall.

For the first time I could open up to someone who actually cared; and she listened. I heard her talk about her school studies and basketball; listening to her frustrations and victories; and for once I was actually interested.

The next two and a half hours flew by as we ate pizza and drank beer together. The fact I was underage didn't seem to matter to Raylene; she ordered the beers and we shared a glass together. We sat in a dim far booth away from the crowds and just talked; it felt so natural.

When Raylene glanced at her watch, I knew it was time. With a heavy sigh I asked the waitress for the tab. I slipped cash for the bill and a tip inside the folder while Raylene sat and watched; a small smile on her face.

"You know I've never had a guy buy me dinner" she said softly as we settled in for the drive back to Mel's.

"Then I consider myself very lucky" I said quietly.

"You mean that don't you" her voice came in the dark cab.

"Very much, it's been one of the best nights of my life" I answered honestly.

"I have to admit...mine too" I felt her slender fingers twine in mine as my hand rested on my thigh. "Thanks Dawson" she said in a soft voice.

"No, I should be thanking you" I gently squeezed her hand.

I pulled into Mel's driveway and got out, coming around to the passenger side. I opened the door and held out a hand. Instead Ray slid out and down into my arms; her back against the seat. We were hidden beside the truck with the open door blocking the house side.

"You know he's going to ask you if you kissed your date good night" she said in a quiet voice.

"I can't lie" I shook my head.

"You wouldn't be, if you did it" her voice came softly to my ears.

"Raylene..." I felt my throat tighten.

"Be a man Dawson" she murmured softly.

We were standing in that tight space, so close I could smell the strawberry in her shampoo; and yet with only a dim porch light casting a shadow; only her large brown eyes shone as she watched me.

Something inside me, maybe it was the smell of her hair or the touch of her hand. I moved without thinking and closed the final inches as my lips found hers in the dark.

"Mmmmmmmm" I felt the tremor of her lips as she moaned softly.

This was no sibling kiss; this was a dates' kiss. It was soft and yearning; with a hidden hunger in the background. By the time we pulled apart I could hear her labored breathing and I fought to catch my own breath.

"Sorry" I mumbled.

"Dawson, do me a favor" Raylene's voice filled the darkness. "Do that again" she said softly.

I didn't even think about it, I just responded. I pulled her into my arms, wrapped them around her. Her firm breasts pressed against my chest as my lips found hers a second time. This time, my tongue slid into her mouth; to duel with hers. I felt her hands slide up my back as she held tightly; her throat thrumming as she moaned into our kiss again.

By the time we separated again; we were both gasping for breath.

"This is dangerous" she whispered softly.

"It feels so right" I countered.

Without a word Raylene slipped around me and walked to the front door of the house. She stopped and looked back at me as she held the door knob.

"I hope you pick a good movie" she said back to me, and then disappeared into the house.

As I drove home, seven inches of steel hardness between my legs; Raylene stood inside Mel's house leaning against the front door.

"And...how did it go?" Mel asked.

"He was the perfect gentleman" Raylene said softly. "And I'm soaking wet" she looked up at her friend with fear in her eyes.

Dawson knew he only had a few more weeks before prom, so the time crunch made me him push a bit faster than he wanted. He informed his parents he had another date the following Saturday.

His father had given him the scowl when he said he had not bedded the 'girl' on their first date.

"Get with it boy" his father had scowled.

But when he told them it was a movie date, his father applauded.

"Perfect" he told Dawson. "The old hand can land anywhere in the dark and who is to blame."

Dawson felt his stomach flip. After the ending of their first date; the kiss he and Raylene had shared was far beyond anything a brother and sister should. Could he really make a pass at her in the dark theater? How would she react?

Those thoughts never totally went away; even when he pulled into Mel's driveway the following Saturday. The last week he and Raylene had hardly seen each other; she was finishing her exams and he was trying to get every extra he could in at his job. He hadn't even heard her leave the house earlier in the day, and he had wanted to see how she would dress.

As he stood inside the entryway waiting, Mel just watched him. He could feel butterflies in his stomach, he shook himself inside; this is your sister for God's sake; he thought. He turned at the sound of steps and when Ray walked around the corner, he couldn't stop the surge of blood that filled his cock even if had wanted to.

Her hair was done up in softer curls and lay splayed out on her shoulders. This time she wore a touch of make-up and her lips were glistening a light pink. She wore a light blue button blouse and the first two buttons were undone, giving just the hint of cleavage from her breasts. The material was thin enough Dawson could just barely make out the hint of her bra through the fabric.

She was wearing a mid thigh leather skirt that hugged her hips and flowed with the curve of her ass like a black velvet second skin. Dawson trailed his eyes from her firm supple thighs down her tanned legs to the sky blue painted toe nails in open heels.

"Holy fucking God" he whispered softly.

Raylene turned and looked at him, hearing the soft murmur.

"You're beautiful" Dawson choked out.

"Thank you" Raylene gave a shy smile as she walked past him to the front door. As she passed by him her voice barely above a whisper, hit Dawson like a load of bricks. "And you're hard" she said calmly.

Helping her climb into the truck again, he couldn't tear his eyes from her. Raylene looked down at him with a glint in her eyes.

"Is it that bad" she asked.

"No, it's that good" Dawson admitted.

They rode in silence in the growing dark until Dawson could barely discern her tanned thighs next to him, but the image was burned into his brain from his continuous peeks when Raylene shifted in her seat or crossed her legs.

Picking the movie had been one of the easiest things Dawson had done. He and his sister had almost the same likes and dislikes; so picking the new Marvel show The Black Panther had been a no brainer. He pulled into the theatre parking lot and found a spot. As he turned off the engine, Raylene reached out and gripped his hand in the dim light of the parking lot.

"We've always been honest with each other" she said softly.

"Yes" Dawson said slowly, not sure where this was going.

"Are you hard...right now?" he heard her ask in a small voice.

"Yes" Dawson couldn't deny it, and she was right they had always been honest together.

"Why?" Raylene asked as she turned and looked at him.

"Don't ask" he choked out. "It's wrong."

"Is it because of me?" her voice sent a tremble through him.

"Yes" he could barely speak the word.

"It may be wrong, but it still feels good to hear" she gave his hand a gentle squeeze before she released him.

Dawson walked around the truck and opened the door. He extended his hand but this time Raylene turned to full face him, and as she prepared to slide out of the seat; her thighs parted. Dawson couldn't help himself, it was like a magnet pulling his eyes; and he glimpsed the color of purple lace between her firm thighs just as she started to slide towards him.

For the first hour of the movie Dawson was in pure hell. He barely saw much of the show as every time Raylene crossed her firm muscular thighs; his eyes were drawn to her legs. When he glanced up his heart rate nearly doubled. Didn't she only have two buttons open? He thought. Now three fasteners were free and the top half of her breasts were clearly in view in the flickering light of the screen.

He had hoped that the distraction of the movie would help his raging hard cock subside; instead it was the opposite. He lost track of how many times her fingers gripped his arm; and even once she reached out and gripped his thigh only inches below his groin. The constant contact and the sight of her exposed flesh; kept a steady flow of blood pumping into his engorged cock.

Finally, Dawson couldn't stand the tension and suspense. The words of his father rang in his ear; you could always blame it on the dark, he thought. He reached out and took a drink of his soda; replacing it in the holder, instead of resting his hand on the armrest, he let his hand drift to the side and let it come to rest on the smooth skin of Raylene's thigh.

For a brief second he felt her tense under his touch; and then she relaxed. He had expected her to yell at him; but her face stayed locked to the screen. He was more shocked when she made no attempt to stop him as his hand slowly drifted over her thigh.

Her skin was warm and soft under his fingers; and Dawson marveled at how smooth her legs were. He began to explore the length and width of all that bare skin; each inch sending more blood into his already painful hard cock. When his hand bumped the edge of her skirt, Raylene reached down and gripped his wrist.

Oh God she's going to yell at me, Dawson thought. Instead he was shocked by her soft words.

"What color are they?" Raylene asked in a soft whisper; her eyes never leaving the screen.

Dawson knew then she had seen him peeking when she got out of the truck. His immediate reaction was to deny; to claim ignorance. But it was the thought they had always been close that changed his mind.

"Purple...lace" he whispered back.