Sexploits Ch. 05: Kaitlyn

While Katie may not be the hottest girl I have had sex with, nor is she the only or even the first girl with whom I have enjoyed many depraved, exhilarating sexual experiences, the genuine, unadulterated friendship we share coupled with the boundless, sexual exploration we enjoy together certainly makes her one of my favorite people with whom to spend my time. Of course, neither one of us intends for this type of relationship to reasonably go on indefinitely, but while we're still pretty young, we've certainly mastered having a good time when it comes to sex, thanks in large part to Katie's willingness and eagerness to try anything at least once.

Katie wasn't blessed with the petite frame that is common among most of the girls I've been with, but she works hard to keep her roughly 5'7" body in shape. Beside, her slightly thicker frame brings with it big boobs and a nice ass, traits I have come to enjoy immensely over the past couple years. And although her pale skin, rosy cheeks and light freckles weren't features I generally considered to be part of my type, she certainly knew how to use them to her advantage with some makeup and a little effort. Plus, I'd never been with a blonde before, or a girl with blue eyes, until I consummated with Katie, and they say blondes are more fun, right?

The beginning of Katie and my sexual journey was merely the culmination of one of the lowest points in my life, actually. However, it turned out to be not only one of my most memorable sexual encounters, but it opened the door to some of the wildest stuff a guy could ever experience. To begin, I will focus on how Katie and I initially moved past being simply friends to the dynamic we have today.

For years, Katie and I had been just platonic friends. Over time, I suspected that Katie was attracted to me, but that attraction was never mutual until one especially frigid night in February a few years back. That night, I let my guard down just long enough to enjoy that first episode of surprisingly wild and passionate sex with a girl whom I failed to even notice sexually prior to that event.

What had changed my mind about Katie were my personal circumstances during that point in my life. I had just been jerked around and led on for three months by a girl with whom I thought I'd have a meaningful, lasting relationship. The breakup was so abrupt and executed so poorly by my now-ex that it immediately plunged me into a near depression, and the stress of my job coupled with the unrelenting bitter weather during that season may have pushed me over that edge.

Several good friends were there to support me during that stressful time, and Katie was one of them. In reality, I hadn't always gotten along with her perfectly, though; she was kind of selfish, immature and borderline annoying at times, but, in her defense, she was only 21 years old at the time, several years younger than most of my friends and I. I kept in mind that she'd grow up and that I shouldn't let incidents of normal immaturity affect our friendship. Regardless, she was very sweet and encouraging throughout those couple weeks during which I struggled, something that I can't stress enough, because she truly was a wonderful friend to have at that time.

Maybe it was my desperate need to do anything that made me feel better during that rough patch (while remaining a responsible adult), but I began to see Katie differently. Also, after another failed attempt at a serious relationship, I was ready to give up on that notion and focus on just having fun with people I trusted. Whatever the specific reason, one day, I asked Katie if she wanted to hang out with me that coming Friday night. She happily agreed and followed up by asking if we'd be getting dinner.

"Hey, what the hell," I said. "Let's make it a date."

There were plenty of factors that easily could have made my first date with Katie a disaster. Work ran late, so it was already dark by the time I got home. The temperature was 6 F when I walked out to the car to make my way to the agreed-upon restaurant. It was so cold that I wanted nothing more than to go back inside my warm apartment and just avoid what I was expecting to be an awkward evening anyway. Finally, it began to snow pretty bad once I was about halfway there, naturally, making the conditions all the more stressful.

To my surprise, however, Katie and I had a lovely time right from the start, actually. Immediately, I was stricken with how good Katie looked. For the first time, I thought she was hot -- not just attractive, but bend-her-over hot. Her red dress caught my attention right away, presenting her body perfectly. The garment was short, going maybe halfway down her thighs, and low-cut, showing off just enough cleavage so as to still not be whorish. Not only did it accentuate the features I already admired, such as her red lips, big boobs and round ass, but it flipped those qualities I had previously overlooked: the garment hugged her frame flawlessly, drawing me to her hips and creamy thighs; her rosy cheeks glowed just right with the dress as well as with the makeup she wore; and her pale skin contrasted with the the clothing in the most lovely way. In addition, her blonde hair hung straight, almost touching her shoulders, with just a slight curl at the end. A lock of it hung cutely over the side of her face but carefully avoided obscuring one of her bright blue eyes. I also noticed her high heels and jewelry -- all black -- that worked well with the outfit.

Confused is probably the best way to describe my feelings as Katie and I were led to a table. I'd never really minded having Katie around but, like I said, I was more likely to feel annoyance with her than arousal. In that moment though, I was thankful for the poor lighting in the restaurant; otherwise, the proverbial roll of quarters in my pants would have been more obvious. It didn't matter though; I'd later find out she'd noticed my boner anyway and had been quite pleased by the discovery.

On purpose, I'd chosen a more casual location to get dinner, but it hadn't stopped Katie from dressing up, obviously. Initially, I hadn't wanted my strictly platonic friend to take this date too seriously, but now I was glad I hadn't discouraged her too much. I know there were a lot of personal factors weighing on me that perhaps clouded my judgment, but my goal changed before our order was even taken. No longer was I hoping for a simple pleasant time with minimal awkwardness. Now I absolutely couldn't help but desire to have sex with Katie before the next sunrise.

When I complimented Katie on her dress, she smiled and blushed a little. She seemed happy that I not only noticed her attempt to dress up for me but that I liked it as well. As I perceived that she was accepting my advances, I began to flirt with her more and more shamelessly throughout the course of our dinner. As the meeting progressed, Katie responded more giddily to my new-found attraction for her. Her several drinks, which I must admit I didn't discourage, only lowered her inhibitions. I'd been concerned in the past that Katie might have had a bit of a drinking problem, so I didn't want to take advantage of her, but I figured a couple drinks to help her get the edge off would better ensure some adult fun later, which I suspected we both wanted.

Getting to the point, I invited Katie to come back to my apartment when we walked back into the cold, snowy night. The undesirable conditions of the roads made my invitation all the more gentlemanly too, not that I had much doubt that Katie's mind was going down the same path as my own. Undoubtedly, the girl would readily accept the opportunity to spend the night at my place if what I was inferring was correct.

It wasn't all that late when we got back to the apartment, but the roads were so bad that nothing else was really worth the trouble. I clarified for Katie that she could sleep over, especially since the weather was bad and she had had maybe one drink too many at dinner. I offered her my bed so she would be comfortable, but not wanting to put any real pressure on her, I suggested that I sleep on the couch. Those aforementioned drinks probably had something to do with her response:

"The couch?" she said with a tone that assured me she'd had too much alcohol. "You're going to fuck me, right?" She immediately caught what she's said. "Oh my gosh, I'm sorry! I was just kidding. I'm sorry," she stuttered before I could respond.

I smiled and looked over at my blonde friend, thinking about what the rest of the night had in store. "No," I said, "you're right: I won't need the couch tonight." Katie's face went from embarrassment to delight instantly. I wondered if her heart was beating as hard as mine.

We hurried into the apartment, fighting through what was now a snowstorm. Once we were inside the warm lodging, we slipped out of our jackets and shoes before I led Katie to the bedroom. If I'd had something for her to drink, I would have offered, but she didn't need it anyway.

As Katie sat down on my bed, I was across the hall in the bathroom, psyching myself up to nail my friend. It was crazy how just a few hours ago I would have never seriously considered actually having sex with Katie and now there was nothing I wanted more. Once I felt prepared, I made my way back across the hall.

Maybe because she was tipsy or maybe because it was just her way of getting to the point, but Katie was under my covers when I came into the room, a wide smile on her face, that strand of curled hair hanging over one eye. The next thing I noticed was that the dress, along with a black set of panties and a bra, was on my floor. I had expected some sort of striptease but now suspected that she was a little self-conscious of her body. It was no matter, though, as I just followed suit, quickly taking all my clothes off and turning off the lights before joining her naked in the bed.

As my eyes adjusted to the darkness, my cock was rock-hard in seconds as I prepared to screw my friend. Once I could see better, I climbed up on top of Katie and hovered over her, propped up by my arms. I realized right away that Katie had nothing about which to be self-conscious. While I hadn't really been attracted to her prior to this moment, I'd also never seen her naked before. Maybe it was the way the pale light filtered through the blinds on her creamy skin, but I found her body very sexy in that moment. Her large breasts jiggled a bit as her flat stomach rose and fell with her breathing. I was captivated and more than ready to enter her. First, though, I wanted to taste those perfect tits.

Katie giggled a bit and cooed as I leaned forward and put my lips around her left nipple. I sucked gently on it and then traced around her boob with my tongue, causing my friend to squirm beneath me. Then I switched to her right breast and gave it the same treatment. The longer I did it, the louder Katie moaned and the more abrupt her movements became. Eventually, my tongue traveled down her front as I licked her stomach and finally arrived at her clit.

"Oh please," Katie whined. Using one hand, I located Katie's sweet spot and spread it open a bit before putting my tongue back on her body, this time pushing the tip into her pink pussy, which was already wet with anticipation. Katie slapped her hands on the sheets and gripped them tight as she felt me begin to lick her pussy.

I could hardly believe what I was doing! I ate Katie out for a few minutes, varying my force and consistency but all the while making her squirm and moan. I lapped persistently at her twat, which grew increasingly wet the longer I pleasured it. I released any remaining inhibitions and just let myself go. Before long, we were more than ready to fuck, but first I wanted her to return the favor of oral treatment.

Perhaps it came from being good friends before the sexual interest developed or maybe because I was really just asking for her to return a favor, but I had no difficulty asking Katie for exactly what I wanted. She was happy to comply, too, switching with me on the bed so that I was on my back and she was on her knees, the blanket still on top of us as she scooted between my legs. Next, she took my engorged cock in her hand, looking at it with wide, greedy eyes as she began to stroke it with her soft hand.

"I've wanted this cock inside me for so long," Katie said as she looked into my eyes, now beating me off. I sighed with pleasure, not responding to her but just watching as she rubbed my cock before lowering her head and opening her mouth. I exhaled loudly as Katie slid her hand to my balls and took my raging boner into her warm, wet mouth.

For the next few minutes, Katie's head bobbed up and down as she held my cock in place, sucking the entire length and making it slick with her saliva. I gripped the sheets and pressed my head hard against the pillow, moaning every few seconds to affirm my friend who was pleasuring me. It wasn't the best blowjob I'd received in my life, but Katie certainly knew her way around a stiff cock.

Katie slurped on my dick for a few minutes, occasionally looking up at me with those bright blue eyes as strands of her hair fell in her face. Actually, I was surprised at how adept she was at sucking cock. Katie had always seemed like one of those good girls who didn't get a lot of sexual action. The way she blew me off made me only more excited to move along to the main event.

Next, Katie crawled up onto me. In response, I rolled over, flipping her into her back and quickly spreading her legs. Katie grinned and looked down, watching as I used one hand to hold my wet prick while my other hand searched for her pussy. When I found it, I noticed right away that it was practically dripping.

Nerves returned as I moved forward with fulfilling my new-found desire to plug Katie. After all the shit I'd been hit with over the past month, I almost felt relief from the fact that something was going to feel good for a change. Once I wedged my tip into Katie's damp twat, I slowly pushed forward.

As I thrust into Katie, I stopped every inch or so and watched her reaction. Each time I did so, she closed her eyes and moaned. She told me how good I felt inside her, and I continued to push forward until my cock was to the hilt. At this point, we both exhaled, and I lay down on top of her, fully inside my blonde friend who had never looked hotter.

Katie instantly wrapped her arms around me, and, with my head over her right shoulder, I began to thrust in and out of her. Her pussy was wet and tight around my cock as it pushed back and forth into the blonde. I felt Katie's ankles press against my calves, her heels digging into my muscles as I ground deep into her and then pulled back and thrust in again. We moaned in unison as we adjusted to each other's bodies, which were gloriously united. What had seemed so unlikely going into this night felt so right that it seemed it was the only possible outcome all along.

As I made love to her pussy, Katie pushed me up, pulling my head away from her shoulder and over her face instead. Then for the first time, we kissed. It struck me how I'd commenced having sex with her before even kissing her. I'd never before done those things in that order, but I'd also never had a fuck buddy before, which is essentially what Katie was to me in this moment. Even as I made out with her while I fucked her, I wasn't looking for anything romantic. Although I wasn't necessarily avoiding some sort of relationship, fun with my friend was all I was seeking. Beside, I knew a little passionate kissing didn't endanger our newfound physical relationship, and those lovely lips and that skilled tongue of hers turned out to be very enjoyable.

Still taking my cock deep inside her hard and steadily, Katie pushed me onto my back, causing us to both roll over. I desisted from thrusting into her but managed to keep my cock stuffed firmly inside, albeit barely, as we moved. Now on top of me, Katie pulled away, sitting up. The blanket fell down to our legs, and now I was really able to take in Katie's naked body, the sweat on her boobs and stomach glistening in the little light that was reflecting off the snow through the window. I couldn't believe I'd never realized how this good friend of mine had a such a body made for fucking.

Blonde hair fell into Katie's eyes again as she leaned forward, putting both hands on my stomach and grinding her pelvis on my cock. She grinned at me, and I smiled back as I ran my hands up and down her thighs. Then she started to slide up and down my cock, slowly at first, but it wasn't long until she was riding me steadily.

I moaned, and Katie gasped as her boobs and hair rocked up and down while her body did the same. Katie steadily fucked me, tightening her pussy around my member as she rode me. While Katie didn't have the best body that had ever gone for a joy ride on my dick, she did have the biggest tits of any girl I've slept with, so I rather enjoyed their bouncing as she eagerly took me back inside her over and over again, causing the bed to creak beneath us as she slid faster and faster up and down my member. Watching the blonde babe so deftly polish my knob with her tight, wet pussy made me beyond thankful I had gone into this evening with an open mind.

I alternated between squeezing Katie's boobs and simply watching them bounce as she fucked me for a little while longer. After a few moments of intense intercourse, my friend asked for me to put her on her back again and ravage her until we both came. Before tonight, I would have never expected such language from this girl. Even as she fucked me, it still shocked me a little, but I complied. By now, my balls were longing for release anyway, though my heart and mind would have been happy to fuck Katie all night long.

Again being careful to not slip out of Katie, I rolled her onto her back and resumed fucking her missionary style after just a brief stint of reverse cowgirl. I got right to pounding Katie's pussy as she held onto my hips, pushing each of my thrusts as deep into her as possible. I moved slowly and deliberately at first, watching Katie's eyes flutter shut each time my balls touched her taint as she reacted to the pleasure. Then I moved faster, thrusting in and out of her quickly, nailing her to the mattress beneath her, which creaked each time Katie was pounded into it.

My head now over her shoulder again and her arms and legs wrapped around me, Katie cried out as I slammed into her over and over. Our bodies leaked sweat that mingled together as our flesh slipped and slapped against each other. I could tell by Katie's movement and moaning that she was nearing an orgasm, so I pumped even harder into her, which made her cry out until she said, "I'm cumming all over your cock!"

From that point on, I pushed hard into Katie's pussy again and again to work myself up to an orgasm of my own while she writhed beneath me. Just after Katie's orgasm started to subside, I pulled out to avoid erupting inside her and instead hovered over Katie as I stroked myself, trying to hold in my climax for as long as possible so as to blast her with some hard spurts. Katie was panting and I was straining as we both awaited my finish.

I wanted badly to cover Katie's boobs, so I aimed for them and finally let loose. My burst was so hard that the first spurt overshot Katie's tits completely and hit her clean in the forehead, streaking down her left eyelid and cheek. I have to say, it was a fortunate misfire, as it was really hot to watch Katie's face get blasted with cum. Katie laughed between breaths as the next shot hit her chin, and then the rest of it successfully doused her boobs. By the time I was finished, my man juice was streaming down to her stomach as it streaked across her tits.

We were both now completely relaxed and, in a sense, relieved to get the sexual tension out before it really had a chance to mount. Katie would spend the night, but we didn't come together again that time. In fact, it was actually a couple weeks before we'd fuck again. I was OK with it because Katie turned out to be just the fuck buddy I needed at that point in my life. Neither one of us required anything serious at the moment. For now, sex was a fun activity for the two of us to enjoy when we had the time and opportunity without the stress and pressure of a relationship. I assumed a setup such as this one was destined to be short-lived, but I was determined to enjoy it for however long it lasted.