Kyle’s Story

Authors Note:

This story had been requested from a few in the comments of 'Old Wounds' and at first I wasn't sure how I felt about it. Though, the more I thought, the more the idea struck my fancy so I sat down to write it out.

A big, big thank you to JFS1212 for editing and beta reading this story. He took something that was riddled with errors and made it grammatically sound.

This piece is a standalone story and can be read as such, but some of the background information may make more sense if you've read my series: Old Wounds.

All characters engaged in any form of sexual activity are over the age of eighteen.

Also, I'm trying actually writing these on a Doc and uploading the file now instead of just writing in my notes app then copying it to Lit, so if the formatting gets messed up, I apologize and will fix it. If it's messed up you can either come back to the story when it's fixed, or soldier on and try to deal with the formatting. Hopefully it uploads as I've typed it though.

**

Fuck my brother. I mean that in the nicest way possible. He really is a great guy, my best friend in all likelihood, but still, fuck him. Not fuck him because he's an asshole, or he stole my leftovers from the fridge, but because he stole the woman of my dreams from me.

Ok, that's not fair, he didn't steal her exactly, he just up and married her sister. Now the girl I'd been pining over since I learned what women were was my sister-in-law. At least I think that counts as my sister-in-law?

Matt did absolutely nothing wrong. He and Katie were truly meant to be together, and I was nothing but happy for them. Them being together just sort of left me in a shitty spot, not that I ever had a chance with Allison anyhow.

Either way, it didn't matter. Thinking about Allison while Cassidy's lips were wrapped around my cock just didn't seem right at all. Not that I really cared if it was right or not. Let me rephrase that, I didn't care if it was right or not, because Cassidy certainly wouldn't have cared if I was thinking about Allison.

I should probably explain. I had just turned eighteen, like literally just turned eighteen about seven minutes ago. Cassidy was one of my good friends, but not a girlfriend. She was almost a year older than me and graduated last year, but still lived at home so her not being in high school anymore didn't tamper with the friendship.

Yesterday Cass surprised me by offering to give me a blowjob the second I turned eighteen. I figured it was a joke, but immediately after she said it I knew she was serious. I also figured she didn't mean 'the second I turned eighteen' literally, but that we'd meet up at some point on my birthday and she'd do the deed.

"I'll also fuck you too, but I know you've said you wanted to save that," she said nonchalantly.

"Uhhh," I replied, drawing it out in hopes actual words would form in my mind.

"Just head then," she shrugged as if it was no big deal.

It really wasn't a big deal, to her at least. She had a very open view about sex, and while I certainly wouldn't call her a slut, she did indeed call herself one, and didn't take offense when anyone else did either, whether they were joking or serious. 'Sex is just sex, if I want it, I'm going to get it' is what she'd always say. She wasn't wrong though, she certainly could get it whenever she wanted. She was an unbelievably sexy young woman.

I was born at six fifty-two in the morning, so as it turned out, I was set to turn eighteen, if you went by the minutes and not the date, on my way to school, so you can imagine my surprise when my phone rang at six thirty, and even more surprised when I answered it to hear Cass say she was serious.

"You can be late to school once Kyle," she giggled. "My dad just left for work so I've got the house to myself. Stop by and let me be the first to properly wish you a happy birthday."

"As it happens, I'm just getting ready to pass your house," I chuckled nervously, not wanting to question her and risk the good fortune that was all of a sudden coming my way.

Cass and I never flirted, never hooked up, never did anything other than just be friends. That's not to say I didn't find her dangerously attractive, I most certainly did, I just didn't want anything with her. I was too hung up on Allison.

Cass didn't want anything with me either, so it worked out. She also knew about my deep attraction to Allison, so the thought of us doing anything never really crossed our minds.

"Good. Just come right in, we're going to do this right. It's your first blowjob, and also your birthday. I aim to make sure you never forget it," she said sultrily, hanging up the phone before I could respond.

Being late to school didn't really matter to anyone but my mother. It was the first week of my senior year anyways, so nothing was even really going on yet. I was old for my grade, the second oldest of everyone actually.

By that point I was at her driveway so I swung my truck up the gravel path and slid it into neutral, killing the engine and slipping it back into gear so it didn't roll. I took a deep breath and popped the door and hopped out, making my way inside.

"In my room," she called from upstairs. I'd been there a few times so at least I knew where to go.

I kicked my boots off at the door and headed for the stairs, my heart beating heavily in my chest with every step. I don't know why I was nervous. I wasn't even doing anything. Sure, I'd never even done anything more than make out with a girl, but this was Cass. She knew what she was doing, and she couldn't care less about if I popped off too quick, had a micro dick (which I didn't), or anything else. To her she was just giving me a birthday present.

I was able to somewhat get my nerves calmed by the time I reached her door. When I opened it my heart pounded even harder and I felt light headed, though for a reason completely unrelated to being nervous.

Cassidy was standing next to her bed completely naked. I'd seen all kinds of porn, but any of them couldn't hold a candle to the view she was giving me at that moment. If she had a mind that centered on sex, she certainly had a body that was built for it. While it was true I never really wanted anything with her, that doesn't mean I didn't fantasize about it. Often.

She was about five four and weighed maybe a buck thirty, but I'd be willing to bet at least twenty of those pounds were held in her tits with another ten in her ass. I didn't know her exact bra size, or even how bra sizes really worked, but I'd guess they were at least a few letters above DD. Her impossibly narrow hips flared out into what was likely the greatest heart shaped ass I'd ever get to lay my eyes on. She really did look like someone used AI to create the perfect sex symbol.

"What time is it?" She asked with a demure smile.

"Uhhh," I stammered, snapping my arm up to look at my watch. "Six fifty-five."

"Well I didn't hit the second on the money, but this is close enough," she all but purred as she strode towards me, her hands deftly undoing my belt.

"Cass," I began.

"Shhh," she cut in. "I'm going to ask you two questions and then make a statement depending on your answers."

"Ok," I breathed in frustration as she'd stopped short of undoing the button on my jeans.

"Do you want me to suck your cock?"

"I do," I stated plainly.

"Will this mess with our friendship? You know I don't want you romantically. I just want to give you a good birthday present and have a little fun."

"Of course it won't."

"Then you're going to be very late to school," she smiled. "Because I'm going to suck you dry, then you're going to do whatever you want to me. I know you don't want me romantically either, but let's be honest, I know you find me hot, so we're going to enjoy this for what it is. When you've had your fun and get hard again, I'm going to make you cum again. I'm not sure how yet but I'll figure that part out. After that, if you still want more, I'll make you cum again. Hell, I'll make you cum as many times as you physically can if that's what you want. You can cum anywhere, any way you want. We don't have to have sex, but it's on the table."

"Holy shit Cass," I groaned, greatly turned on by the combination of her words and her nudity.

She didn't say anything in response, and didn't wait for me to say anything else either. Instead she just pulled my belt out of the loops in one swift motion. The belt coming free, coupled with the way she was standing caused my Letherman to fall and bounce off her bare foot.

"Fuck," she exclaimed, the slight pain in her voice undermined by a laughing tone. "I forgot you wear that damn multitool."

"You ok?" I chuckled, making sure she was ok even though the situation was sort of funny.

"I will be once I have your cock down my throat," she said, pushing me back onto the bed.

I let out a laugh at that, and she did as well. That little mishap took the nervousness and tension I was feeling out of the air. It really was just a friend doing something fun and nice for a friend.

Before I was even completely settled on the mattress she was tugging my jeans and underwear down my legs. I heard her let out a slight gasp as my rock hard cock sprung free, no longer restrained by my clothing.

"Well that's fuckin' perfect," she said with a smile.

She must have seen the confused look on my face because she went on.

"I ain't a size queen. I'm smart enough to know that too big a dick can be a problem. This'll do just perfect, and it's easier for me to really blow your mind."

Now I wasn't small mind you, but a rather average size from what I'd seen and read. I was about six and a half, maybe seven inches and decently thick, but proportionate to the size. I wasn't ashamed of it, as I figured it was more than some, and more than enough to get the job done, but I was surprised she'd called it perfect, as I knew she'd been exposed to a number of them, all shapes and sizes. Trust me, I'd heard more than I wanted to from her.

She was religious about getting tested though, so even though she'd been around, I knew for a fact she was clean. If I had any doubts I wouldn't be doing this.

I guess she wanted to put on a show as well as make it amazing for my first blowjob, so she slowly crawled up the bed, dragging her tits up my legs and abdomen. When they brushed against my cock I let out a frustrated groan, suddenly wanting so much more.

"I should have asked you this earlier," she breathed into my ear once she'd made it all the way up my body, "but do you want me to just suck your cock, or do you want the full experience? Making out, roaming hands, all that fun stuff? I don't care either way."

In lieu of responding I cupped her cheek with my hand and guided her lips to mine. I had a steady girlfriend earlier in high school, so even though I was inexperienced in anything sexual, I got a good many hours of practice with kissing. I considered myself pretty good at it too in my humble opinion.

I added a little more pressure to the kiss and let my free hand drift to her bare hip. This seemed to flip a switch in her and she moaned into my mouth, attacking me with vigor. Apparently she was frustrated with the lack of skin to skin contact because she started clawing at my shirt, trying to rip it over my head, which was impossible because she didn't want to break the lip lock.

"Here," I said, breaking the kiss, having to physically nudge her back because she just followed me as I went to pull away. In a swift motion I pulled the shirt over my head, and before it even hit the floor she pounced back at me.

Her tits mashed against my chest and my hands flew to her amazing ass, squeezing hard and pulling her into me. She just moaned and dug her fingers into my hair, trying to pull me further into the kiss. She ground her hips into mine, causing sensations I'd never known to shoot through my cock, causing me to groan and pull her closer.

She pulled away from my lips, rather reluctantly by the feel of it, and began to trail kisses along my jaw and to my neck. The warm wetness of each kiss turned me on even more, and I knotted my fingers from one hand in her hair and used my other to pull her even tighter against me. For two people with no romantic interest in each other, this was fucking hot and very sensual, even if it was heated and urgent.

Her kisses trailed down my collarbone to my neck, and I let out a moan when she flicked to tongue across my nipple. I guess I didn't imagine that would feel good but I was pleasantly surprised. She giggled cutely but kept kissing her way down my chest and stomach, finally reaching my waistline. I figured I was in for at least a few minutes of teasing torture since she took a lot of enjoyment out of teasing in normal day to day life, but she surprised me when she immediately went for it, licking from the base to the tip then diving down and taking me all the way into her throat with one smooth motion.

She held me there for a long moment, looking up at me with lust filled eyes. Then she somehow started to massage me with her throat muscles. That alone was almost enough to make me blow my load but I surprised myself when I was able to hold back.

Cassidy then withdrew until just the tip was left in her mouth and swirled her tongue over the head and gently gripped the shaft. After a moment she slowly started to move her hand up and down and let go of the tip with an audible pop.

"You don't need to try to hold back. We've got all the time we want and I'm sure I can manage to get you hard again," she purred, adding a wink before she dove back down and resumed her task.

I never wanted to cum so bad in my life, but at the same time I wanted to savor this, at least for a few minutes. It was my first blowjob after all. Cassidy, however, seemed intent on making me pop as quickly as she could. I knew it wasn't because she wanted it to be over, but because she took pride in her skills and wanted to show me how good she was.

Her head was bobbing up and down quickly but not rapidly as her tongue swirled the head at the top, and stroked the shaft when she went down. Her hand was also pumping in time with her head, and the difference in pressures and sensations was driving me absolutely crazy.

The entire time she never took her eyes off of me. I didn't know it as I'd never had a blowjob before, but apparently I was a sucker for eye contact. While this amazing woman was pleasuring me I started to question why we didn't want anything more together. We fit together rather nicely and she was obviously a ten out of ten with an amazing personality and sense of humor to boot. Regardless, something was just missing there, even if I couldn't put my finger on it, and the desire to have her as a girlfriend just wasn't there, and I know she felt the same.

I cursed myself for letting my mind wander and instead just focused on the amazing blowjob I was getting from this amazingly sexy woman. I couldn't push back the pressure building in my balls for much longer so I tangled my fingers in her hair and moaned from the intense pleasure.

"I know I said you can cum anywhere you want," she said, letting my cock slip from her mouth while still slowly pumping my shaft, "but for your first blowjob I'd really like to swallow it, you know, so it's completely a proper blowjob."

"Godddddd," I moaned as her hand circled around the head. I couldn't manage any more of a response than that so I just gently guided her head back down towards my cock.

She flashed me a wicked smile then resumed trying to suck my soul out of me. I couldn't keep my hips from bucking up to meet her, but as she'd already demonstrated, she wouldn't be choked or gagged by a cock suddenly sliding down her throat so it didn't phase her at all.

I felt the pressure building up and my hand tightened in her hair. She must have taken that as me letting her know I was close, or she felt me starting to swell in her mouth, because she doubled her efforts, moaning around my cock as she was clearly turned on by this as well.

"Cummmningggg," I growled as I felt the first spurt of my orgasm shoot into her mouth.

She just sucked harder and kept bobbing up and down at a now rapid pace. I tried my best to keep my focus on her, I really did, but black spots started to form in my vision as my whole body was wracked by the most intense orgasm of my life.

I didn't pass out, of that I was sure, but I felt like I was pretty close to it. The black spots cleared from my vision rather quickly, in time for me to see her sit back on her heels, cup her amazing tits in her hands, and make a show of swallowing my seed. If that wasn't the hottest thing I'd ever see in my life, it would definitely remain top five no matter what.

"Holy fuckin' shit Cass," I breathed when I was finally able to find words.

"Good first blowjob?" She grinned, full well knowing the answer.

"If there's a blowjob out there that could top it, I'd probably die and go to heaven," I chuckled, still trying to catch my breath.

"You know my views on sex, so today is all about you and making your dreams come true. Any fantasy you've ever had I'd probably be willing to make a reality," she smiled before adding, "unless it's too crazy."

"I ain't dreamt up anything wild so don't worry," I assured her. "Hell this is all new to me so I've really only thought about the basics."

"Well, what do you want now?" She asked.

I'd always been of the mind to save my virginity for a special time. That didn't necessarily mean marriage or even with the love of my life, rather just a situation with someone I cared about, not just some rushed attempt where the only thing that mattered was losing it. I decided then and there that this was worth it.

Cass was a good friend and a great person. Obviously we cared about each other a great deal, even if it wasn't romantic. She was insanely sexy, and to top it all off, it was my birthday. I figured it was definitely meaningful enough and I'd without a doubt remember it fondly for the rest of my life.

"I want to make you cum," I said finally.

"This is your day though," she pouted.

"I know. I want you to teach me how to pleasure you. I want to hear you scream," I said, surprising myself with my boldness.

"You do that and I'll be liable to mount you and fuck you into oblivion Kyle," she breathed, clearly turned on from what I'd told her.

"Maybe that's what I want," I grinned before pulling her into a deep kiss and letting my hands explore her body.

"It won't take long," she moaned as my middle finger parted her slit, finding it absolutely drenched, almost to the point of actually dripping. "I'm so fucking worked up right now."

"Good," I murmured as I lightly nipped her neck before gently sucking on it.

"Ohhhhhhhhh," she purred. "Slip a finger in, YES!"

She cried out as I slid my digit into her sopping wet hole. I'd watched a lot of porn and read a lot of erotica, so I had a good idea of what to do, I'd just never had the chance to put it to practice.

I kept kissing and lightly sucking her neck, collarbone, and earlobe as I slowly worked my middle finger in and out of her, curling it up slightly every now and then as I did so. I knew what the g-spot was and where it was supposed to be, so I thanked all the stories I'd read when I heard her cry out when I found it.

"Use two fingers," she instructed. "Ohhh fuck yesssssss."

I moved my free hand up to play with her tit, using my thumb to circle around the nipple as I massaged the heavy globe. She clasped her hands around my head and neck, pulling me into her as I did. I figured she must have sensitive nipples, so I increased my attentions on the nub and was again rewarded with sounds of pleasure from her.

Without any warning she tensed up, then started shaking slightly. I kept playing with her nipple as my other hand was fingering her, scraping against her g-spot with everything thrust of my fingers.