High School Hooker

After dinner Kara went up to her room while I helped my Mom with the dishes. Then I went to my room to do my homework. A couple of hours later I finished and decided to get ready for bed. It was still only around nine o'clock but I figured I would take a shower and get ready for bed, then put a movie on in my room and watch that until I fell asleep.

I took a shower and brushed my teeth. With a towel wrapped around my waist I headed back to my room for the night. When I walked in I was surprised to find my sister laying in my bed on her stomach. She was propped up on her elbows texting on her phone. What really made me stop in my tracks though was that she was laying on top of the sheets in nothing but a small white tank and lacy bright blue boyshort panties.

The material was nearly see through and it hugged her ass tightly. The neckline of her tank hung down low, exposing the top of her perky tits to my view as well. I couldn't help but let my eyes roam across her body, her feet kicked up behind her as she focused on her phone.

"Hey!" She greeted when she looked up at me.

"Hey..." I replied. I closed the door behind me and walked over to my desk. "What are you doing Kara?"

"Just texting while I waited for you."

"Waiting for me like that?" I asked, motioning toward her half naked form.

She looked down at her cleavage and then back at her half naked ass. "What? You have seen WAY more of me by now then this..." Then she sat up and repositioned herself on my bed. Crossing her legs in front of herself and planting her hands on my bed behind her. Causing her tits to press forward against her tank, her hard nipples poking through the material to my view.

"Yeah but...not like this, not in person..." I argued. She was right though, I'd seen about as much of her as I could through the camera, but this was different.

"What so you're ok with watching me fuck and jacking off over me in a video but panties and a top are crossing the line when we are at home?" She teased.

I just shook my head. "No, it's not that...I mean..."

Kara laughed, she was having fun with this.

"It's alright Bri...I'll get naked for you if it makes you more comfortable..." She started lifting up her shirt until the bottom of her perky breasts started to show. "You can even jack off if you want..."

"Kara! What the hell...I didn't mean..."

Then she collapsed onto her back in my bed laughing. I shook my head and grabbed some clothes out of my closet. I should have known she was fucking with me.

"I'm just playing Bri...common, its my pajamas. No big deal." She said when she finally calmed down.

"I know...you just surprised me thats all." I said.

"Well I would think that a hot half naked girl in your bed would be a nice surprise..."

I stood by my dresser with my clothes in my hand and looked at her expectantly. "Ummm...you gonna let me get dressed?" I asked when she didn't get up to leave.

"Go right ahead, I don't mind." Kara smiled and just continued to look at me while she lay back in my bed.

"So much for privacy..." I said. I kept my towel wrapped around my waist as I pulled my boxer briefs on under it, keeping my crotch blocked from my sisters view.

"Oh you're no fun..." She complained and brought her phone up in front of her face again.

I pulled on some shorts and a t-shirt then sat down in my chair. "So I assume you came to talk to me about today?" I asked.

"Yeah I guess...I know you probably want to."

"Yeah, I do. So what was up with all that? You were barely talking to me and then you drag me out to watch you again..."

Kara sat back up and crossed her legs indian style in front of herself. This gave me a nice view of her barely covered mound. I could nearly make out the shape of her pussy through the thin material.

"Uhem..."

I hadn't realized my eyes wandered down like that, and she surely caught me starring, but she just smiled. "You HARDLY had to be drug out there..."

"You know what I mean. Last week you could have killed me for what I did and today you welcomed it."

"Well that was last week and today was today."

"Okay...so what was different...?"

Kara didn't answer right away and looked like she was thinking about what to say for a moment.

"Okay..." She started. "I really could have killed you last week. But I was really mad then too. I was furious that you had betrayed my trust like that."

I looked down, still somewhat ashamed with myself and waited for her to continue.

"I didn't watch the videos for a couple of days, I thought it would just make me that much more upset at the situation. But when I finally did, I wasn't mad at all..."

"What do you mean?" I asked.

"I watched them and it didn't upset me...it turned me on!" She looked at me for a second, seeing my eyes widen slightly. "Seeing myself in the videos, watching myself get fucked and doing everything that I did made me horny as hell...I even masturbated to them myself..."

"Seriously? You did?" I was really confused, I hadn't expected her to say that.

"Yeah, really. I didn't realize how hot that could be."

"But...weren't you mad that I...you know, jacked off to it..."

Kara thought about that for a few seconds before responding.

"Actually no. I was mad that you snuck the camera in there and that you were hiding it from me. But it actually didn't bother me that you liked it. You're a guy, sister or not it's going to turn you on to see a hot girl having sex."

"Yeah, I guess you're right."

She nodded. "To be honest it was flattering to me. You know my reputation, I don't try to hide it. I like to have fun and I don't care if people call me a slut, I am a slut. Yeah guys pay to watch me finger myself sometimes but I don't just act like I enjoy it. It really does make me horny watching them jerk off over me. And knowing that I have that same effect on you...well, it gave me a different perspective on some things..."

"How so?"

"That you could have really fucked me over...that you could have blackmailed me...but instead you didn't..."

"That was the original plan actually...blackmailing you..."

"I figured. But you didn't. So I wasn't mad anymore, really I wanted you to keep doing it. I wanted you to watch me again. I knew you wouldn't though so I had to come up with a plan to get you out there and I knew I'd have to be direct."

I still wasn't completely sure I understood but at least I knew her reasoning for it.

"Okay so...what about Lilly then? Why pay $500 for me to fuck one of your friends?"

Kara started laughing. "Are you complaining?"

"No! Not at all..." I shook my head and smiled. "I guess I kind of understand about recording and watching you...even if it is a bit weird, but how does hooking me up with her turn you on?"

Kara looked into my eyes and her lips curled into a cocky smirk.

"Actually...that wasn't about turning me on. That was about satisfying my curiosity...and it was about payback..."

"Huh?"

"Let me show you. Come here." She pointed for me to go sit next to her on the bed. I did and she grabbed her phone. She swiped her way through some files and turned on a video. She handed me the phone and then sat back while I watched.

The screen brightened and after a few seconds I recognized it as Lilly's room. Suddenly it made sense to me. I watched the screen patiently until I saw Lilly and myself enter the room. I skipped ahead a few minutes to see her knelt down in front of me with my cock in her mouth. I skipped ahead again to see her riding me, her tits bouncing as she slammed herself up and down on my cock.

I looked up as Kara stood up off the bed. She stepped in front of me and climbed into my lap, straddling me, her barely covered pussy pressing against the hard on I didn't know I had until then. I was too shocked at that moment to react one way or another.

"So..." She said, resting her forearms on my shoulders. Her perfectly round ass pressing snugly against my crotch. "Now I have a video of you too...so I got my payback..." She smiled and ground her hips slightly, causing her pussy to slowly rub against my raging erection. Then she leaned forward and whispered in my ear. "And I satisfied my curiosity of whether or not the rumors were true that you had a nice, big cock..."

My eyes popped open wide and I suddenly regained control over my body. I pushed Kara to my side onto the bed and stood up, a huge bulge in my shorts. She laughed at my reaction and sat up again.

Before I could say anything she spoke.

"Brian calm down. I said I had new perspectives on things. What I realized other than it turns me on to be watched like that is that I don't see us as off limits to each other...Yeah you're my brother, but that doesn't bug me. I don't want to be with you, as a matter of fact I know about your date with Lilly. I just don't mind the idea of us having some fun together, thats all."

"Us...together...like...?" I stuttered.

Kara stood up and stepped right into my personal space. "Yes Bri. Us. You and me. Just for fun."

I looked at her face for several seconds while I got over my initial shock. My mind was going crazy thinking about what she was saying.

"I don't know Kara..."

She smiled and brushed her hand against my cock as she walked past me toward the door.

"Okay...don't stress out thinking about it, I just wanted you to know where I stood." She opened the door and began to leave but before she did she looked back at me. "But don't worry big brother...if you decide you do want me...i'll give you the family discount..." And with a wink she closed the door.

Needless to say, I didn't sleep much that night.

Neither Kara or I brought up the subject again the rest of the week. I tried to keep busy and focus on other things during the day at school but at night I tried to wrap my head around what she had said. Strangely, I was feeling more and more like I would be okay with it as well. 'I already know I'm attracted to her. Hell, I jacked off while watching her...' I reasoned to myself. The idea of incest still just didn't seem completely ok though and I found myself trying to talk myself out of being attracted to my sister.

Luckily I didn't go crazy thinking about it all day and night. Lilly and I texted a lot that week and hung out during lunch a couple times. It was a welcomed distraction from my internal dilemma. We had plans to go out that Friday night and I was looking forward to it.

Friday finally came and I was in my room getting ready for my date when Kara came in.

"You look handsome Bri!" She complimented from behind me. "Lilly is gonna like that outfit."

"And how do you know that?" I teased as I turned around. I stopped in place when I saw that Kara was all dolled up for a date herself. She was wearing a small black dress that fit tightly against her skin. The thin straps led down to a low cut neckline, displaying some very enticing cleavage. The hem of the dress couldn't have gone more than a few inches below her amazing ass.

She walked up and began straitening my collar for me. "I know...smart ass...because its making ME wet just looking at you..."

I shook my head and chuckled to myself. Kara finished messing with my collar and winked at me before stepping back and sitting on my bed. Crossing her long legs and leaning back on her hands.

"Thanks..." I said and looked over myself one more time in the mirror. "You have a date too?"

"Yeah."

"Cool, have fun!" I looked over to her.

"Oh I will..." She replied mischievously. I just laughed.

"Bri...have you thought about what I said at all?"

I knew she was going to ask this sooner or later. "I have..."

"And...?"

I took in a breath and let it out slowly before responding. "I'm not sure yet...we can talk about it later okay?"

She stood up and walked over to me. "Okay." she said with a smile and kissed my cheek. "Have a fun date!" She said and left.

"You too!" I called after her.

It was really dark out, with almost no moonlight shining through the trees. But that would also make it more difficult for anyone to see us if they drove up.

"Oooooohhh...ugh ugh ugh..." Lilly moaned over and over as she rode up and down on my cock. Her tight red dress was bunched up around her waist and my hands were gripping her ass tightly. Pulling her down harder onto my throbbing cock. She hadn't worn panties so it had been easy for her to just climb onto my lap after I parked my truck along the dirt road leading up to a local trailhead.

Our date had been great. We went to dinner and talked the entire time. Lilly was fun and energetic and we had a good time flirting and chatting for a couple hours. After that we climbed into my truck and left. I had suggested going to get dessert but she ducked her head down into my lap and said she was in the mood for something else.

"Where should we go?" I had asked while she unzipped my pants and started to extract my cock.

"I don't care, just find somewhere..."

It was a miracle I had been able to keep from driving off the road while I made my way to the trail. All I could focus on was Lilly's wet mouth engulfed around my cock as she took it into her throat. She sucked and licked it the entire time, fingering herself as she did until I finally put the truck into park.

I didn't even have my seatbelt off yet when she started pulling me toward the middle of the bench seat so that she could mount me. Her pussy was already soaked and I slid into her easily as she began bouncing her firm teenage ass up and down my thick shaft.

Fifteen minutes and two screaming orgasms later and she was still bouncing up and down on it. I could feel the sensitivity of my cock increase as it slid in and out of her tight, velvety pussy. Her perky tits pressed against my chest as she leaned into me, her arms wrapped around my neck as she fucked herself up and down on my pole.

Lilly was breathing hard from all the exertion and I could feel a light sheen of sweat on her skin as I ran my hands up and down her side. I reached both hands up and took her breasts into my hands, squeezing them gently. She leaned back and ground her pussy against me with my cock fully embedded inside her.

"You like that tight little pussy baby?" She teased in a sultry voice. A wicked little smile on her gorgeous face.

"Fuck yeah..." I groaned. Feeling myself getting close.

She leaned in and kissed me. I watched her face contort into a look of carnal pleasure just inches from mine as she began to cum again.

"Oh fuck...oh fuck...oh fuck..." She cried out loud. Her pussy began to convulse around my cock as she came. I took hold of her ass in both hands and pulled her hard against me. She rocked her hips back and forth, grinding herself hard as her orgasm came and ripples of pleasure shot through her. Her pussy spasmed around my cock, setting me off as well.

"UGH..." I grunted loudly as the first thick shot of semen entered her pussy.

"Ooohhhh fuck yes! Oh cum in me baby!" She cooed when she felt my cock begin to pulse and empty my load into her.

"Uuugghhh..." I groaned as shot after shot of cum ejaculated from my cock and filled her cunt. She was so tight that it felt as if she were milking every drop out of me with her beautiful vagina.

"Emmmm..." She moaned. "I was waiting all week for that..."

I chuckled. She climbed off my lap once we both came down from our orgasmic highs.

We were both quiet for a minute. Then I looked over to my pretty date. Her face seemed to have a slight glow to it and she smiled pleasantly. Her eyes met mine and she giggled.

"What?" I asked.

"That's the first time I've given it up on the first date..."

We both broke into laughter at that. I pulled some napkins from my glove box and handed them to Lilly so she could wipe up the cum leaking from her pussy. We both cleaned up the best we could and fixed our clothes. Then she slid close to me and kissed me.

"Thanks for a nice date sweetie!" She said when she finally pulled away.

"You're welcome, hopefully you'll want to go out with me again."

"I'd very much like to go out with you again!" She smiled.

We sat there awhile longer, kissing and holding each other.

"Can I ask you a question?"

"Of course." She smiled.

"You don't have to answer...and I'm not judging or anything..." I started. But she cut me off.

"You want to know if I hooked up with anyone this week." She stated more than asked.

"Sorry, I was just curious..."

"No it's ok, I understand. But no, I haven't." She smiled. "I didn't think it would be right since we had a date, at least not until I knew how you felt about it and if we were going to keep seeing each other."

"You didn't have to do that though, I wouldn't have gotten mad or anything." I tried to assure her.

"Oh I know, but I wanted to." And she kissed me on the cheek.

"So are we going to keep seeing each other?" I asked.

Lilly's smile beamed brightly. "Duh!"

I couldn't help but laugh.

"But I think we should just keep it casual and fun for right now. We should just date, not rush into a relationship." She continued. "If you are okay with me still doing what I do for now then I will and we will see what happens between us. That okay?"

I thought for a moment about that, I really didn't have a problem with it. So I smiled and nodded 'yes'.

"Good!" And then she pressed her lips to mine again and proceeded to try and suffocate me with her tongue.

Shortly after that I drove Lilly home. She was a bit worried that I would get upset if she kept seeing her "clients" while we were seeing each other. I assured her that I was ok with it.

"Like you said, casual and fun. We will see where things go from there. If we decide we want to be more, we will discuss it again then."

That seemed to make her happy. "Goodnight sweetie!" she said as she kissed me goodbye for the third time in her driveway. Then she went inside and I got back into my truck and headed home.

I was in a great mood as I walked into my house and up to my room. As I lay in bed that night I thought about how fun the night had been with Lilly. I wondered how things were going to turn out between us in the future. I knew she was going to still see the two "clients" that she had but that was it. She wasn't going to go out with anyone else but me. Most guys I know wouldn't be able to handle that but I guess I wasn't like most guys. It was kind of a turn on that the pretty little innocent friend of my sister had such a naughty side that only a few people knew about. I also knew that if I wanted her to stop that she probably would.

'Vbbbbtttttt'

My phone vibrated on my bed next to me. I saw that I had a new text and opened it.

"New Message: Lilly - Night cutie! See you soon!"

I smiled and replied 'goodnight' to her. I set my phone down and closed my eyes again, falling asleep shortly after.

The next morning I was woken up way earlier then I had planned on. "Brian get up, just for a minute." I heard my Mom calling up to me.

My eyes were barely cracked open as I walked downstairs to the living room. My Dad was loading some bags into his SUV and it looked like my parents were going out somewhere.

"Sorry Honey, I just wanted to make sure you didn't need anything else for the weekend before we left. Theres cash in an envelope on the counter for pizza one night and any snacks you guys want to pick up."

"Huh?" I mumbled semi coherently. Still not fully awake.

My Mom just shook her head and laughed. "Nevermind, I already told all of this to your Sister. Your Father and I are heading out. Our weekend trip remember? We will be back Monday night."

I had completely forgotten about this. I yawned and nodded my head in understanding.