Kaitlin's Dare

So far it had been just another ordinary summer day, having graduated high school and just turning 18 I was relaxing before starting college in the fall. My sister, Ashley, who had finished her first year of college, had a few of her friends over to hang out by our pool.

As I got some water in the kitchen I noticed they were all egging on her friend Kaitlin to fulfill her dare. I admit I had my eye on her for some time. She was tall and drop dead gorgeous; she had dark brown hair to her chest and light brown eyes. The short skirt she was wearing displayed her long perfectly toned legs and her tight T shirt showed off her shapely hips and her set of 34Cs. She had been over the house for years and I always had a huge crush on her but could never work up the courage to ask her out. After all, at almost 21 years old she was a junior in college, my sister’s friend, and let’s not forget… very, very hot.

What happened next was unforgettable, Kaitlin suddenly shouted out, “Fine! I’ll do it!” before jumping into the pool fully clothed. As her friends laughed and applauded her actions, Kaitlin thrashed around in the water before stepping out of the pool. My jaw almost hit the floor as I realized she wasn’t wearing a bra!

“Damn girl! Go borrow some of my clothes!”Ashley said giggling as Kaitlin approached the glass door to the kitchen. I could easily make out her perfect breasts through her thin T shirt.

She stepped inside the kitchen and was shocked to see me standing there. After seeing my obvious discomfort, she smiled and asked, "Hey Jimmy... could you show me where I could get a towel."

Setting down my glass, I replied, "Sure Kaitlin...not a problem." I couldn't help but catch the little smirk on her face as I led her into one of the bathrooms. As I entered the bathroom, Kaitlin came in behind me.

“Thanks Jimmy!” Kaitlin said cheerfully, putting her hand on my arm as I handed her a towel.

I couldn’t help but through her wet T shirt at her flat stomach that had a winged tattoo next to her naval and her perfectly formed breasts that were topped with small pink nipples.

When our eyes met, she smiled at me and I was overcome by her beauty. Her light brown eyes, slightly upturned nose, and full cheeks made her drop dead gorgeous.

Feeling my cock start to rise, I stammered, "So I guess I should leave you here to...." I was cut off by Kaitlin’s mouth as our lips met for a slow and passionate kiss. Her tongue quickly found mine and started dancing around in my mouth as she dropped the towel and wrapped her arms around my neck.

Breaking the kiss, Kaitlin stared into my eyes as she turned to shut and lock the door. I stammered, “Oh my god Kaitlin...what was that for?"

"I dunno, Jimmy, just something I've been dying to do to you for a long time! And judging from that tent in your shorts I see whenever I’m over I know you have too...haven't you?" Kaitlin asked before she started to slowly kiss down my neck to my shoulders. I groaned as I felt her lightly bite my shoulder as she caressed my back through my shirt and her wet breasts crushed into my chest, soaking the front of my shirt.

"Oh Kaitlin...I've been dreaming about this moment for so long," I whispered as I felt her hard nipples pressing into my chest, my whole body tingling as she slowly kissed back up my neck.

When our lips met again, we kissed passionately as our hands began to tear at each other's clothes. Kaitlin reached for the bottom of her shirt, briefly breaking our kiss as she pulled it up and over her head, tossing it aside as she brought her lips back to mine. When her hands started to pull at my shirt I briefly broke our kiss as I pulled off my T-shirt and tossed it to the side. Our kiss intensified as she pulled down my gym shorts and I unbuttoned her skirt. Kaitlin let her skirt fall to the floor before kicking it aside. I kissed down to her breasts and lightly bit her nipples as I pulled down her panties to join her skirt on the floor. Kaitlin gently pushed me away before softly saying, “Your sister will be suspicious if we're gone long… shall we get down to business?”

I could hardly believe I wasn’t dreaming as I stood there looking over her perfect body. From the smooth skin of her long and toned legs, to the perfect curves of her hips leading up to her round, supple breasts. As my eyes reached her beautiful face, her pretty brown eyes locked onto mine. Kaitlin smiled and whispered, "Mmmm I know that look… time for us to have a little fun..." Placing her hand on my chest she continued, “But not a fucking word to your sister… got it?”

As I nodded in agreement she turned to face the mirror, braced herself against the counter and looked back over her shoulder. Shaking her per fact ass, she said softly, “Mmmm come on then… fuck me Jimmy.”

Reaching down to grab my cock, I guided the head along her sopping wet lips before I thrust deep inside her pussy. Kaitlin groaned as she took in the feeling of my hard cock thrusting inside her.

"Ohhhhh fuck!" Kaitlin cried out as my throbbing cock slid all the way into her, stretching her tight cunt. Kaitlin pressed hard onto my cock and slowly began to grind her hips in circles, getting used to the size of my throbbing cock. I leaned forward and cupped her breasts, eliciting a moan as I began lightly teasing her nipples.

“Mmmm I love that! Your sister would kill me if she saw us,” Kaitlin moaned before she leaned back and wrapped her hand around my neck, drawing my lips to hers for a passionate kiss

"Oh Kaitlin! This feels so fucking good!" I said softly as I took in the feeling of Kaitlin’s hot, wet, tight, silky smooth pussy gripping my cock as I began to thrust into her in a faster and harder pace.

“Oooo Fuck! Smack my ass and pull my hair!” Kaitlin begged as I rammed into her.

“Oh fuck! Harder! Jimmy HARDER!!” She cried out as I started smacking her ass with one hand and tugging on her hair with the other. She was definitely a kinky girl, squealing with delight as I ravaged her body. I couldn't believe how good her pussy felt around my cock, it was like a vice, squeezing my cock closer and closer to orgasm.

"Mmmm I fucking love this," she cried out loud as she fucked back into me. Her right ass cheek was feeling red and swollen, but she loved it every time I laid my hand into her.

She threw her head back and stared into my eyes as I thrust in and out of her cunt. Grinning deviously she cried out, "Ohhhh god! Were finally fucking! After all those years… Ashley’s little brother… Oh my god yes! Were so fucking bad!"

I pulled out momentarily as she turned to hop up on the counter, wrapping her legs around my waist and her hands around my neck, our lips met again for another hot passionate kiss. Kaitlin screamed into my mouth as I thrust back into her, mercilessly pounding into her weeping cunt. My eyes feasted on her body as she leaned back, her perfect breasts bouncing with each thrust. Suddenly, her orgasm hit and I could feel her cunt squeezing the hell out of my cock as she rode out her orgasm. I could see the look of near agony in her face as she slowly ground her clenching pussy into my cock.

As I stared back at Kaitlin's face, she looked so sexy with her wet, matted hair tossed everywhere. As our eyes met, Kaitlin grinned and wrapped her legs tighter around my waist. “Mmmm looks like somebody’s gonna cum soon! Bet you're dying to cum inside me aren’t ya?” she teased as I grabbed her hips and she began to grind her pussy harder and harder into my thrusting cock.

"Oh fuck...Kaitlin... I'm gonna cum!"

"Mmmm that’s it! Cum inside me Jimmy," Kaitlin gasped.

I groaned as I felt my balls tighten and I shot a massive load of cum deep inside her hot pussy. Kaitlin shuddered with pleasure and dug her nails into my back as she felt my cock fill her with my hot, white, and sticky cum. Our lips met again and we kissed passionately as I came down from my orgasm.

Both of us panting with exhaustion and release, Kaitlin leaned back against the mirror, her breasts heaving as the both of us grinned with delight in the afterglow of our release.

"Mmmm I needed that… nobody to fuck around here and I’ve wanted to do this for so long Jimmy... I always thought you were pretty cute," Kaitlin whispered as she lightly kissed my neck and ear.

"Me too Kaitlin... I’ve been dying to fuck you," I replied as I slowly pulled my cock out of her dripping pussy.

"Oh-shit," she cried softly, as my cum began to run down her slit to her ass and all over her thighs. Giggling she continued "Jesus, hunny, how much did you cum? I'm leaking cum all over the place!"

Running her fingers along her slit she scooped up some of my cum and licked her hand clean. “Mmmm,” she said softly, grinning wide. “We taste good together baby… can’t wait for next time.”

“Me too Kaitlin, next time your over we should have an encore performance.”

Rubbing her hands up and down my chest Kaitlin smiled and said, "Mmm I second that...but I better get out of here before your sister comes looking for me...” Hopping off the counter, Kaitlin wiped up her thighs before wrapping the towel around her. She continued, “But don’t be sad… we got a whole summer to catch up on lost time... see ya soon!”

After sharing one last kiss, Kaitlin darted out of the bathroom and into my sister’s room. I couldn’t wait to see what the summer had in store for me.