My Best Friend Kaytlin


Thanks to HeyAll for editing this story.


I wake up from a knock on my window. I check my clock and sigh when I see it reads 2:53 AM. I hear the rain hitting my other window hard. In tired exasperation I wonder who could be at my window this late at night and in this weather.

I swing my legs over the side of the bed and rub my hands over my face, trying to wake up a little bit. As I stand up I run my hand through my thick brown hair, trying to make it look messy but failing.

I’m not the most good looking guy on the planet, I know that. I don’t have any muscle tone, even though I am strong. I have a little bit of chub on my stomach that I can’t seem to get rid of no matter how many times I work out. I’m about 5’11” and have dark green eyes. I don’t have much of a tan, mostly because I get sunburnt so easily that I avoid going outside for long periods of time. Looking down, I see that I’m only wearing pajama pants that are a little loose on me. I shrug and walk over to my window to lift the blinds up.

Standing there in soaked clothes is my best friend, Kaytlin. We’ve known each other since we were in elementary school, and now we’re both at that awkward stage of being in between high school and college. We’re both eighteen and are going to the same college in the fall.

She smiles at me through the glass and taps on the window again. I roll my eyes at her and smile back, then I lift the window open.

“What’re you doing?” I ask her.

“Oh, nothing,” she answers, laughing lightly. I love the sound of her laugh. “Just hanging out in the freezing rain. Now let me inside, dork.”

I step aside and reach my hand out of the window so she can grab it. She hoists herself up and climbs into my room, dripping water onto the carpet.

“Do you, um, do you think I could borrow some dry clothes Julian?” she asks, looking down at herself as I shut the window quietly. I don’t want to wake up my roommates.

She’s a fairly attractive woman. She’s about 5’2″ with wavy brown hair that reaches to her ribcage. Her skin is slightly tan and her eyes are a vibrant blue color. She has slightly smaller than average boobs, but a phenomenal ass. She’s pretty skinny, altogether she can’t weigh more than 120 pounds, max. She’s wearing a light grey t-shirt, and because it’s soaked through, her nipples are clearly visible. Her black leggings must be sticking to her legs, which cannot be comfortable.

“Yeah of course,” I walk to my closet to grab her an oversized shirt to wear. “So, why are you at my house at three in the morning?” I ask her sarcastically, slightly annoyed that she woke me up.

“I was just bored. I needed someone because Dereck and I just broke up. I wanted to annoy you. Take your pick,” she laughs, obviously not too upset about her and Dereck splitting up. She did nothing but rave about him – how he treated her terribly, ignored her, etc.

“You and Dereck broke up?” I ask, trying to sound concerned. But I’m not worried about it; he was an ass and she never really liked him. I honestly don’t know why they stayed together for a year and a half.

“Are you okay?” I ask, not waiting for the obvious answer to my last question.

“I’m more than fine, it’s about time I left that loser. You and I both know that he never deserved me,” I chuckle slightly. That’s the understatement of the year.

I turn around to say something else about what an ass Dereck is and see her pulling down her leggings to reveal a light blue lace thong. “Woah, Kaytlin. You could’ve warned me you were stripping before I turned around,” I say, shutting my eyes and holding the shirt out to her.

“Calm down Julian, it’s not like I haven’t changed in front of you before,” she replies. She’s right, she used to eryaman escort change in front of me often. Then again, that was years ago; before either of us had gone through puberty or developed a sex drive.

I decide to not say anything, but keep my eyes closed. I don’t want to make it obvious to her that I’ve been attracted to her for a long time now.

“Okay, I’m done changing. You can open your eyes now,” she laughs.

When I open my eyes I see that she’s laying on her side with her elbow propping her head up on my full sized bed that’s pushed into a corner in my room. She has the remote to my TV and is searching through Netflix.

“What’re you doing? Your hair is getting my pillows all wet,” I laugh with her.

I walk over to my bed and climb behind her. I pull the blankets up over us and prop myself up on my elbow too, so I can see my TV screen. She’s looking through drama films and I roll my eyes behind her. Of course she would watch a romance drama. She picks out one that looks really cheesy and presses play.

She leans over to set the remote down on my nightstand and her shirt lifts up over her hips, showing me her bare ass. I quickly look away, not wanting to get a boner while she’s right next to me. She lays her head down on the pillow and watches the movie, and I decide to try and fall back asleep. I have work tomorrow and I don’t want to be tired.

I am just falling asleep when she scoots up against me. “I’m cold, this shirt isn’t very warm and my hair is wet.” she says, her ass rubbing against my dick.

‘Does this woman realize what she’s doing to me?’ I ask myself. I scoot away slightly so she’s not pressed against me, “How about I go get you a pair of pants?” I offer.

“No, I just want to cuddle to warm up. I like cuddling, it’s relaxing,” she says calmly. She scoots back up against me and when I try to move away again I hit the wall. She has quite literally cornered me.

“Well, okay. But don’t move around too much. I’m trying to sleep,” I say, more worried about the friction the moving around would cause on my dick than being tired tomorrow.

“Okay, deal. But you have to actually cuddle me,” she replies. She grabs my arm and drapes it over her stomach, then holds my hand. This makes my upper arm lay across her stomach and my forearm rest between her boobs. She’s playing a dangerous game here.

I close my eyes again and try to fall asleep. If I’m asleep, she can’t turn me on.

I’m fast asleep when I wake up from her rubbing her ass against me. “Kaytlin, what are you doing?” I ask annoyed.

“Trying to get more comfortable. I was waiting until you fell asleep but I guess I accidentally woke you up. Sorry,” she says.

“It’s fine. Just re-adjust yourself so I can go back to sleep,” I say. She rubs her ass against me more and squirms under my arm a bit. The friction from her bare ass against my thin pajama pants is feeling way too good, and my hand is resting on her boob. I move both of my hands to her hips and push her away a little.

“I’m sorry Kaytlin, but that’s just, um, the friction is…” I say, trying not to sound awkward but failing miserably.

She turns her body towards me slightly and looks at my face, which is turning red from embarrassment. Then she looks down and sees that I’m getting hard. I close my eyes and wait for her to yell or leave or something.

I feel the bed shift slightly and I think she’s getting up to leave when I feel her hand touch my cheek. I jump slightly from the unexpected touch and open my eyes. Her face is very close to mine and she’s smiling slightly, looking into my eyes.

“I’ve wanted to, um, to do this for quite some time,” she says.

I look at her quizzically, not esat escort understanding. Her face turns red and she moves her face closer to mine until her lips softly press against mine. I’m so shocked that I don’t kiss back, and after a few seconds she pulls away. She looks into my eyes again and her face drops.

“I knew you wouldn’t want me. I’m so stupid. I’m sorry Julian,” she says, lifting herself up to leave.

I grab her arm and pull her back down onto the bed. Before she has the chance to say anything, I press my lips against hers and raise my hand so it’s cupping her cheek. She kisses me back passionately and wraps her arms around my neck. I climb on top of her carefully and deepen the kiss.

“Fuck, Kaytlin. You have no idea how long I’ve wanted to kiss you like this,” I whisper. I let my hand travel from her cheek to her waist to her leg, lifting it up so it’s wrapped around my waist. I move my lips down to her neck and nibble lightly as she squirms underneath me.

She moans and I stop, “You have to be as quiet as possible, my roommates are sleeping. I wish they weren’t here though, because that moan was really fucking sexy.”

“I’m sorry, I’ll try to be quieter. It’ll be hard, you seem to really know what you’re doing,” she whispers back. I smile and bring my lips back down to kiss her neck, leaving small hickies.

She grabs the waistband of my pants and tries to pull them down. “Kaytlin… I-I’ve never done this before,” I say shyly.

“What do you mean?” she asks.

“I’m, um, a virgin,” I confess.

“What about Kelly?” she looks up at me.

“We never had sex. This is about as far as I’ve gone with anyone.”

She runs her hand through my hair then kisses my lips softly, “Well, you’re not alone. I’ve never had sex either,” she whispers. I’m about to ask her about Dereck, but I decide against it. Right now, who cares?

We smile at each other and I let her take my pajama pants off, my hard on springing free.

“Let’s go slow, yeah?” I ask.

She nods her head and looks hungrily at me. I pull my shirt over her head and kiss her passionately. I lean down and feel her boobs against my chest then moan before remembering I’m supposed to be quiet.

“Fuck, Julian. That was hot,” she says.

“You’re hot,” I say against her lips. She giggles softly and kisses my neck, making it really hard for me to not make noises.

We’re both now completely naked under my covers and my cock is resting right by her entrance. “Are you by chance on birth control?” I ask hopefully.

“I got an IUD a little less than a year ago hoping that someone might actually have sex with me,” she replies laughing a little.

“Fuck yes!” I reply.

I kiss her neck and make my way down to her boobs. I put one of her nipples in my mouth and tug on it with my teeth. She grabs my hair and pulls lightly. I smile and kiss down her stomach and when I’ve almost reached her pussy, I detour right and kiss her thigh. She groans quietly in frustration and I move my hand down to lightly tease her clit. She grabs a pillow and puts it over her face then moans into it. I bite the inside on her thigh lightly which makes her moan again.

I kiss and bite down her leg until I reach her foot. I kiss the pads of her toes one by one, making her squirm uncontrollably. I bite slightly when I reach her big toe and she gasps. Then I kiss my way back up, skipping right over her pussy to start my torture down her other leg. I spend more time kissing, licking, sucking, and biting her this time. I want her to be really wet and ready by the time I decide to fuck her.

When I’m on my way back up, I stop at her thigh and suck and bite until there are visible hickies on her. I finally etimesgut escort lick her pussy from bottom to top. She is so wet, it’s unbelievable. I’ve only touched a pussy once before this, and it was with my fingers while she still had her pants on. Kaytlin moans loudly into the pillow and I smile. I love that I can do this to her.

I stick my tongue into her entrance and tease her clit again with my thumb. Her hips buck slightly and I stop what I’m doing. I want her to cum while I’m fucking her. I quickly kiss my way up to her mouth, unable to wait much longer.

Once I’m above her I look her in the eyes sweetly, “So, I’ve heard this hurts. I’m not going to go too slow because that will only prolong the pain,” I say. I push myself inside her steadily and watch her face crinkle up from the pain.

“Oh, ow. That hurts,” she says as she scratches my back.

Once I’m all the way inside her I pause to give her time to adjust to my size, which is torture for me. Her pussy is gripping at my cock and I have to tell myself to stay still, but my hips are trying to move on their own. When her face goes back to normal and she opens her eyes I pull out most of the way then push back in. Soon I have a steady rhythm. Her expression quickly changes from pain to pleasure as I fuck her slowly.

She starts moaning with every thrust so I cover her mouth with my hand. “You have to be quiet Kaytlin,” I whisper, “I know it’s really hard, but you have to try,” I lift my hand off her mouth. I feel myself getting closer, but it’s only been a few minutes. This feels way too fucking good. I pull out quickly, not wanting to push my luck any farther. I pull her close to my chest and flip us so she’s on top. She understands what I want so she lifts her hips up just enough to put my cock back inside her.

She starts bouncing up and down slowly in an uneven rhythm. I watch her boobs while she’s on top of me, bouncing when she pushes herself down.

“Fuck baby, you’re so sexy,” I comment, reaching my hands up to grab her boobs to squeeze and feel them.

She leans down to kiss me, still bouncing on my cock.

“Fuck Julian, I’m gonna cum,” she whispers as she moans.

She shoves her head into the pillow next to my head and cums hard on my cock. When her movements slow down I move my hips into hers, wanting her to ride out her orgasm as long as she can. Her moans slowly die down and I slow my hip movements.

“Holy shit Julian. That was amazing,” she says, lifting her head up to look at me and smile.

I smile with her and pull her close to my chest again so I can flip her onto her back. I start to fuck her slowly again, wanting to savor every inch of her wonderful pussy.

I can feel myself getting closer with every thrust. “You look so beautiful, Kaytlin,” I say, the TV screen flashing light from time to time. She blushes and pulls me in to kiss her tenderly.

The romance and the incredible sensation of being inside my best friend is too much. “Oh, fuck. Kaytlin I’m gonna cum!” I say, getting close to yelling. She reaches up and covers my mouth with her hand in an attempt to keep me somewhat quiet.

It’s not long before my thrusts become more erratic and I feel myself finish inside her newly devirginized pussy. I feel my seed drip out of her while my cock is still inside her. I feel my body start to relax so I fall onto my back next to Kaytlin.

“So, did I do good? Rather, did I feel good?” she says with a giggle.

“You felt fucking amazing, baby,” I reply. I pull her close to me with my arm wrapped around her. She lays across me: her left leg across mine, her left arm across my torso, and her head on my shoulder.

“That’s good to hear,” she replies with a yawn.

“Let’s go to bed, shall we?” I ask, looking down at her. I yawn with her; yawning is so contagious. She simply nods her head and pulls the blanket over us. She cuddles back into me and closes her eyes.

“Goodnight, love,” she says sleepily.

“Goodnight, beautiful,” I reply, drifting off to sleep.

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