High School Hooker - Short Story 1

I held her ass in my hands, squeezing both firm globes and pulling her harder against me. Her dress was soft and thin. I could distinctly feel the lack of panties. For several minutes we simply made out like...well, two horny teenagers.

Eventually, roaming hands led to her dress pulled up over her ass. That led to more kissing which led to my fingers rubbing between her soaked pussy lips. I was correct about her not having panties on and that fact just made me even harder. My cock was straining to be freed from my pants and put into something a lot softer.

Eventually, slow and sensual turned to hot and hurried as Kara stood up and unzipped my pants. I unfastened my belt and flicked the button of my pants open just in time as she was yanking them down. With my clothing now out of the way she straddled me once again and took hold of my rigid erection. She lined it up between her pussy lips and sunk down onto it. Impaling herself on her brothers cock.

The sudden surge of urgency now gone we both relaxed and enjoyed the feeling of my cock filling her tight teenage cunt. The velvety softness of her folds wrapped around me, slowly rising and falling as she rode me up and down.

My hands explored her body gently. Caressing her ass, tickling up and along her ribs, guiding her hips up and down. My movements slow but my grip firm.

Even now, months after our first time, I still couldn't completely believe it. My sister... this gorgeous, slutty, living wet dream...was mine to enjoy.

Her firm, perky tits were shoved in my face...

Her round teenage ass was being squeezed by my hands...as she slid her tight pussy up and down my cock...her brothers cock...

And soon she would once again happily take my incestuous load of sperm into her juicy cunt...

All these thoughts raced through my head and combined with all the physical sensations happening as well, pushed me closer to my third 'birthday orgasm'.

"Feel how soaked my pussy is Big Brother?" Kara teased into my ear.

"Feel how soft and tight it is wrapped around your thick cock...how easily it slides into me when I bounce my ass up and down on it..."

"Emmmm..." I could only moan. She didn't drag it out this time and even though I'd already had a couple orgasms over the past few hours, I was already closing in on another.

Kara kept riding me and kept teasing.

"Are you going to cum in my pussy again Bri...? Going to shoot all that brother cum into me again...?"

She wasn't letting up. Soon she increased her pace, gripping my shoulders tightly while riding me hard. It seemed like every muscle in her body was tense. The only thing moving was her ass bouncing up and down in my hands. Continuously impaling her on my sensitive rod.

"Better hurry Bri...as much as I'd LOVE to tease again...to drag this out and bring you closer and closer to the edge over and over again like this morning...we don't have much time..."

It took a few seconds to click in my brain but I answered with a quick and confused "Huh?"

"Oh, I forgot to tell you...Moms coming home early today..."

A flash of panic hit me and I instantly began turning my head left and right searching for the nearest clock.

But Kara was not about to lose control. She grabbed my head and kissed me hard. Spearing her tongue into my mouth. Then she started riding me faster.

My eyes were locked on hers again as she sat up in my lap, pulling her dress down and exposing her perky tits to my view and squeezing them in her hands.

"Hurry up Birthday Boy...Mom or Dad could be...ugh...home any minute. Oh fuck...how fucking awkward it would be for them to walk in and see their innocent little girl fucking her brother like this..."

My nerves were on fire again and it wasn't just from sex.

"Imagine what they would say...walking in and finding me in your lap..."

"Fuck..." I groaned.

"Emmm...my dress pulled up and your hands squeezing my ass...you hard cock buried inside your precious little sister...buried inside my tight pussy..."

"Fuck Kara..."

"Or even better, coming in right after you came in me...seeing your cum dripping out of their daughters pussy...you sister's bare pussy just oozing your jizz..."

"UGHH FUCK..." I groaned and shot off inside of her. What would have been a weaker orgasm and likely just dribbles of cum at this point had turned into another few thick jets of white semen. Kara squealed happily and kissed me when she felt my throbbing cock spurt into her. Filling her up again.

Never ceasing to amaze me, my sister had once again used her skills to drain as much sperm from my body as she could. I sunk into the couch like a pile of goo, enjoying the post orgasm feeling.

"SHIT!" Kara called out and quickly jumped off of me and to the other side of the couch, pulling her dress back into place and frantically smoothing it out. At that same abrupt moment I realized what had caused her sudden reaction and went right back into my own panic as well.

As if Kara had talked it into existence, I saw BOTH our parents silhouettes through the blinds of the front window walking toward the door.

The risk of getting caught had definitely been fun while we were fucking but neither of us wanted it to ACTUALLY happen!

I urgently and uncomfortably pulled my pants up and tucked my cock away while Kara found the remote and turned on the TV.

I just finished zipping up my pants when I heard the key jiggle in the lock and only had a few seconds to tidy my clothes up enough not to be suspicious.

My parents came in and saw us both sitting there, Kara flipping through the channel guide and me sitting on the opposite end of the couch with my feet kicked up looking as inconspicuous as I could.

I probably had guilt and shock written all over my face but luckily they didn't seem to notice.

"Hey, happy birthday!" My parents both greeted as they put their bags and keys down.

"Hey" Both Kara and I replied. I could still see a faint redness in her cheeks but I don't think anyone else noticed. I also noticed she had crossed her legs rather tightly, undoubtedly to keep my semen from leaking out of her.

Mom came over and kissed my forehead then both her and our dad headed upstairs to change.

"We'll head out in a couple hours for dinner guys." My Dad called back to us. "Pick a restaurant you want to eat at Bri."

When they were both gone I turned to my Sister. We both stared at each other for a second then let out deep breaths of relief.

"Holy fuck that was close!" I whispered, still in disbelief that we hadn't been caught. But she just laughed.

"That was awesome..." She said, standing up. "I need to go clean your cum out of me before they come back down..."

I shook my head.

"Why didn't you tell me they were coming home early Kara? That was WAY too risky..."

Ever the tease she just smiled and rolled her eyes. "Yeah...hot though right?! Besides...you think that was risky, wait until later..."

How did she always manage to leave me dumbfounded and intrigued...shaking my head I decided not to even try to guess what she had planned. I knew it would be good.

Dinner was great. I'd chosen a local steak house, one of my favorites. After all, I was nineteen...a man, and men eat steak...right?

My New York Strip was almost perfect. Medium rare, as it should be, and the steak fries were delicious as well. I enjoyed the quality time with my entire family. Mom and Dad both worked a lot so it was a nice treat to go out and have a great dinner together.

My Dad tipped off the waiter that it was my birthday, as if I didn't see that one coming. They brought out a nice slice of cheese cake for me and sang their quick version of Happy Birthday. All in all, the night was perfect. Quiet, relaxed, and fun.

Later that night I lay in bed talking to Lilly on a video call. She had wanted to say happy birthday and chat for a few minutes while she had the stateroom she was sharing with her parents to herself.

"Dinner was great, we had a really good time" I told her.

"Thats great! I'm glad you're having a nice birthday...and an extra special one from what I've heard..." She teased. "Surprised you're still awake after such an eventful day..."

She giggled adorably and I shook my head.

"I know right. And apparently it isn't over yet."

"Oh you have no idea."

That piqued my interest but Lilly quickly changed the subject. She told me about the couple of port calls they had and how both teenage boys and men alike kept hitting on her anytime her Dad wasn't around. How she missed me and wish she was here to celebrate with us.

"We will have some making up to do when I get back I guess..." She teased.

"Yes we will..." I grinned.

"Too bad you aren't here with me though...there are so many places on the boat we could have snuck off too..."

As she said this I saw her hand come up to the bikini top she was wearing and squeeze her firm tit. Each pass of her hand as she caressed her breast pulled the triangle of red fabric further and further to the side until her hard pale nipple was exposed to me.

I laughed but my eyes were locked on and she knew she had my attention.

"I found this little hidden corner towards the back of the ship earlier...pretty well hidden and just big enough for a couple people to hide..."

She moved her hand to her other breast and pulled that side of the bikini away as well, bearing her gorgeous teenage breasts to me. I didn't say a word, I just lay there and watched.

"It goes to some kind of storage closet or something, but the door was locked." She continued. "Either way, it was out of view from anyone...and your sister had just finished telling me how she was riding you on the couch...how she had pulled her dress up and climbed onto you, and rode you until you came in her..."

She had been pinching and playing with her nipples, obviously aroused, then her hand moved lower. Out of view of the camera.

"I was out on deck sunbathing when she told me all this...that little slut knowing that it would turn me on...so I had to go take care of it, you know?" She smiled.

"Emmm...how did you do that?"

"Well...I knew my room wouldn't be safe so I went looking for somewhere private...and I found that corner...so I went over there and pulled up one of our videos on my phone..."

She was starting to pant slightly as she told me her story. I knew without a doubt that she was touching herself and it all had me rock hard once again.

"I was sooooo horny for you baby...if you had been there with me I'd have just bent over and let you fuck me...but all I could do was push my tiny bikini to the side...like I am now...and rub my clit..."

Her eyes pinched shut and I knew she was getting really turned on but no more than a few seconds later she quickly pulled her top into place, taking away my view of her tits and looked toward the cabin door. I heard what sounded like people coming into the room.

"Ugh...my parents are back, gotta go...Happy birthday Sweetie! MUAH!" And she blew me a kiss. I said goodbye and we ended the call.

I looked over to my clock. It was a quarter til midnight now. My parents had gone to sleep hours ago but I knew Kara had something else planned for tonight. However, without an empty house she was rather limited so I wasn't too worried despite her earlier comment.

I didn't have to wait much longer to find out. Shortly after getting off the phone with Lilly I got a text from my Sister.

"Come to my room..."

"Why don't you come to mine? It's my birthday after all..."

"My room is farther away from Mom and Dads...hint hint..."

She had a point. I got up and quietly opened my door. I tip toed down the hall to Kara's room and entered, closing the door behind me.

"Hey..." she said, meeting me at the door and quickly ushering me inside. She guided me to the bed and pushed me onto it.

"Damn..." was all I could say once I got a good look at her. My unfairly gorgeous sister stood before me in the sexiest lingerie I had seen her in so far. A lacy teal corset hugged her frame nicely and pushed her firm breasts into the most mouthwatering cleavage possible. A matching garder held up sheer teal leggings. Her pussy completely bare and already moist.

"Damn is right..." She smiled and quickly began removing my clothing, having me naked in no time. "I bought this just for you Bri..."

Without another word or allowing a response Kara leaned forward and took me into her mouth. No slow tease or build up, just half a minute of long deep power sucking to take me from semi erect to diamond hard in no time.

Despite the day being full of sex and several orgasms so far, I'd had a decent break since dinner to refresh. Plus my sisters outfit and skilled mouth had me ramped back up quicker than I thought possible.

But her oral attention was not to last. Once she deemed me hard enough, Kara stood and climbed into my lap. Straddling me and guiding the head of my cock between her slick folds.

"Make me cum Bri..." was her only instruction. And I really wasn't given an option either. Kara sunk down onto me hard. She ground her pussy onto my cock, stretching her tight hole around it before raising up and slamming down again. Immediately building to a fast and powerful pace with her hips, literally bouncing her juicy cunt onto me with intense speed and precision.

Her eyes closed, she focused on the sensations starting from her pussy and spreading throughout her body. Biting her lower lip and muffling the sounds trying to escape her mouth as she rode me. Not trying to make me cum quickly but obviously trying to bring herself to an expedited orgasm.

I'd noticed when I first glanced at her that her pussy was already wet and her lips a bit swollen and flushed but hadn't been given a chance to investigate how or why. Now that she was fucking me like this, as if we had been going for hours and with how desperate she was to cum again, I realized she had to have been masturbating for awhile prior to calling me to her room.

As my Sister fucked herself on my engorged cock, bringing herself closer and closer to orgasm, I waited for the indicators. When I knew she was just seconds from cresting over I reached down and began furiously rubbing her clit with my thumb.

"AH! SHI..." She almost screamed out but caught herself, shoving her face into my neck to muffle the sounds. She panted and cursed as her body convulsed on top of me and her pussy flooded with fresh juices. Eventually going limp against my chest.

I grinned in satisfaction to myself for the few moments it took her to recover. Finally, she sat up and took a deep breath, pushing her hair from her face. My dick was still embedded within her and as hard as ever.

"Fucking jerk..." She whispered loudly, a huge smile plastered to her face. She ground her hips in a circle, moaning softly with her eyes half shut as the sensitivity started to subside. When she opened her eyes she had a renewed look. Refreshed and refocused.

"Thank you Bri...now you get your present..."

"Ummm...aren't I already getting it?" I asked, confused.

"Well, sort of..."

Kara lifted herself off of me to my obvious disapproval.

"Oh hush...lay back."

I did as I was told, she smiled and spun herself around into a reverse cowgirl position. Reaching back she guided me into her pussy once again and explained further. However, as she began to talk and pulled her hand away a small round object caught my eye.

About an inch wide and decorated in sparkling teal jewels was what I soon realized to be a butt plug.

"As I was saying...today was fun...but remember how last time I said I wanted you in my ass I chickened out..." She took hold of the teal jewel, slow pulling the plug from her tightest of holes. I watched her tight rose bud expand around the slick silver device as is popped free. Kara gripped her ass cheeks in her hands and pulled them apart, drawing all my attention to her now semi gaping hole.

"Oh fuck..." I sputtered aloud.

"Uh huh...you're going to take my ass Big Brother...you're going to be the first to fuck it..." as she said this she gripped my cock and removed it from her warm pussy, aiming it at my new target.

"You're going to cum in it..."

"Ughhh...." I groaned softly as she sat back slowly, I could feel the pressure of my cock pushing against her overly tight asshole...the delay causing a sense of anticipation within me.

Slick with my sisters creamy pussy juice and whatever artificial lubrication she had already applied, I watched my cock press forward guided by her hand. As if in slow motion her anus spread open, just barely enough to allow my penetration. Then as if a switch was flipped, the head of my cock quickly popped through and into her.

In that fraction of a second my sisters anal virginity, at least from a real cock, was gone. I heard her grimace and her body stiffen at the sensation. I waited patiently until she was ready to go on, fighting back my eagerness to just grab her waist and pull her down onto me.

After a few deep breaths her body relaxed and she began taking a little more at a time. Pushing back and taking half an inch then lifting back up. For a few moments she continued like this, riding just the first couple inches of me while her ass adjusted to my girth. The slowness kept my overexcited and highly stimulated senses from causing my orgasm too soon but the continuous sensation kept me close to the edge.

Anal sex was new to me as well, having only tried the one time with Kara and us not going through with it. But there seemed to be no turning back now. Seemingly determined to follow through this time, my sister gripped her ass cheeks in her hand and spread them wide. The view in front of me was obscene but so fucking hot at the same time.

My gorgeous eighteen year old sister straddling my lap, her bare ass facing me as she lowered herself onto my cock. Rode her brothers cock which was half buried in her ass.

I was starting to quickly understand why guys liked this. It was a different type of tightness then normal sex. An almost rough kind of tightness. This could have been a lot more difficult I realized but Kara had prepared this time. Lubing her ass and spending who knows how long with a plug inside of her, stretching her out.

Finally, Kara inhaled deeply and just went for it. Pressing down harder, allowing my hard cock to slip fully inside of her. Her firm bubble butt finally pressed against my pelvis. Once I was completely embedded she sat still for a moment and we both just enjoyed the feeling.

A minute later she started grinding her hips in slow circles and raising herself up and down slightly, keeping most of my length inside of her while she rode me.

She steadied her hands on my thighs and rocked forward and back. Looking over her shoulder at me I could see small beads of sweat had formed on her forehead, her eyes were glossy but her smile full of accomplishment and pride.

"Happy birthday Bri..."

Now that she seemed somewhat comfortable, I did more than just lie there and let her do everything. I moved my hands to her hips and helped guide her motions. I lifted my pelvis up slightly to meet her and push a little further in and out of her ass.

Eventually she sped up and rode me a little harder. There wasn't going to be any hard pounding for this...at least not for the first time. But slow rocking and short thrusts gave way to long, gentle strokes as the feeling became at least bearable if not enjoyable for Kara.

For me the feeling was nothing short of incredible the entire time but I had enough sense not to rush, knowing that once it was good for both of us it would get REALLY good.

And soon it was.

Kara sat up straight and grabbed her perky tits in her hands. Gripping her two big handfuls of teenage tit flesh as she bounced up and down on my cock. I watched my thick shaft disappear into her nether hole over and over and knew I wouldn't last much longer. However, I think that was also the plan.