Sexploits Ch. 05: Kaitlyn

In the coming weeks, I would find out a piece to the puzzle that might have helped explain why Katie was cool with just being friends with benefits, so to say. It so happened that Katie was actually getting banged by a couple other guys and had been for the past several months, a fact that pretty much floored me. Beside her draw to alcohol, she came off as a pretty upright chick. I had no idea she was kind of, well, a slut and certainly had no clue I was the third one in line for her. I guess, in a certain sense, I truly didn't give her enough credit! I was OK with her loose morality, though, so long as she was safe about it, and she was. Not only were my own boundaries becoming less defined in recent months, but I also found great enjoyment in Katie's friendship and casual sex. In all honesty, the thought of her getting fucked by other guys was pretty hot, though I wouldn't have admitted to it until recently.

Like I said, Katie and I didn't sleep together very often; we just left that door open, a door which we went through on average about only once a month for a little bit. We both had other more significant interests anyway, but every so often one of us would get bored or we'd just be hanging out alone and decide to go back to my apartment and screw for fun. It was a good setup, but I began to really relish in our fuck sessions and found myself thinking and fantasizing about Katie more and more. Before long, she was starring in my most private and most depraved fantasies that I dared not share with her . . . for a while, that is.

You see, not long before I started hooking up with Katie, I had had my first devil's threesome, and since that experience, I became fixated, even obsessed with double penetration. Even though I am and always have been fiercely heterosexual, the thought of sandwiching a sexy girl between another guy and myself became the height of fantasy for me and the hottest pleasure in real life.

As my relationship with Katie progressed and with double penetration often on my mind, it didn't take me long to consider Katie as a sexy piece of sandwich meat as well. In fact, if any other of my female friends were to fulfill my dirty fantasy, I knew Katie would be my best shot, especially considering I was only one of three guys who were playing with her somewhat regularly.

Even though the young blonde wasn't really my type by nature, I wasn't going to be picky when it came to pursuing my perverted desires, since, in my experience, most girls weren't too eager to do what my demented lust craved. Beside, Katie was certainly a cute girl, regardless, and I was growing more and more attracted to her the closer I got to her emotionally and physically.

Like I said, it was almost immediately after our first fuck that my depraved mind envisioned Katie as the center of attention for multiple men. The fact that it turned out she was a bit of a slut only aided my fantasy. A lot of guys in my situation may have been discouraged to continue with a girl like Katie, but her skankiness drew me to her only more, considering that a girl with more than one sex partner turned me on. All of a sudden, Katie was the perfect girl to pursue because it didn't seem like much of a stretch that another one of her guys would team up with me and really have some fun with the young lady. Before long, I felt I had Katie right where I wanted her.

It was late November a couple years ago when I decided to make my move. I had actually been encouraged by an anonymous acquaintance to simply share sexual fantasies with Katie and see how Katie responded. I intended to do exactly as was proposed. This acquaintance even stated that perhaps Katie would suggest all three of her fuck buddies could team up her and make Katie airtight. While I never allowed my hopes to even anticipate such an end, I certainly got excited at that thought!

It had taken a long time to build up the nerve to tell my fantasy to Katie. Being a classic over-thinker, I spent a long time planning out the evening during which I would suggest the subject to be as conducive to my goal as possible. I needed Katie to be buzzed but not drunk when I brought up the topic, the atmosphere had to be casual and the conversation had to lead into my proposition. I didn't want to just bring it up in the car or at my or her apartment, especially since I didn't even know we'd be leaving dinner together. The proposal had to be during dinner in order for me to maintain control of the plan.

Much to my delight and relief, the plan worked out very well. It was a cold evening in November when I chose a restaurant that wasn't very popular so that we'd be less likely to be around people who might overhear us. Luckily, we were seated at a booth with no one else around. What I hadn't considered is that fewer people meant less noise, so there was a higher risk for the situation to be awkwardly overheard. Like I said, I'm a classic over-thinker, and no doubt something was going to add to my anxiety.

We had a lovely night, as we always did when we hung out together. Katie had a few drinks with her dinner, just as I had hoped. The music playing overhead helped drown out our conversation from anyone else who might hear it, which helped calm my nerves as I began to steer the conversation in the direction I intended. The waitress interrupted a couple times, though, shattering my nerves at times, but I persisted.

Finally, my heart leaped as we began to talk about sex. Since Katie and I first banged almost about a year and a half ago, we'd had sex only eight or nine times, actually. Fornication wasn't a big part of our friendship and was something we did only on rare circumstances when we were bored maybe or the events of the day led up to it. In fact, it had been more than three months at this point since we'd last fucked. Sex simply wasn't a topic about which we frequently talked, as surprising as that fact may seem, so I was relieved when it finally did come up. Now that the subject was on the table, I just needed to spit out what I had prepared to say to lead up to my proposition. From that point, I hoped for Katie's cooperation.

"I had a dream about you the other night," I said, though I really hadn't. What I was going to play off as a dream over which I'd had no control was a well thought-out fantasy of mine.

"Do tell!" Katie practically shouted, maybe a little drunk.

"I don't know," I responded. "It was pretty raunchy, and I'm not sure I'm comfortable with it. I'm not sure what you'll think."

"I'm sleeping with three different men," she said, quieter now but flashing a goofy grin. "I'm not one to judge. Try me."

It was do or die time. My heart pounded in my chest, and I focused intensely on not allowing my voice to crack as I told Katie about my "dream" wherein we are at a Halloween party and I walk in on her having sex with some guy I didn't know but was presumably one of her other partners. At that point, though, I lost steam and couldn't continue.

"What happens next?" Katie asked, taking another sip of wine. "Do you join in?"

"Yes, exactly," I trailed off, still unable to get to the point and realizing I was blowing my chance if not for Katie's fortuitous response.

"Do you take turns with me, split-roast me or double-penetrate me?" she offered, blushing a little as she grinned at me. I never did answer that question or get back to my fantasy at all, actually. I took this opportunity to do the asking now.

"Wait," I said. "Have you ever been DP'd?" I had to let go of my glass so that Katie wouldn't see how obviously I was shaking as I determinedly pushed the words out of my mouth.

She laughed. "No. I've just seen a bit of porn, I guess." she said. "I've never had group sex. Have you?"

"I wasn't asking about me," I said.

"But I am," she countered.

She had me where I couldn't really avoid the question anymore, but I was kind of glad because it forced me to get to my point. "A while back," I said, though it hadn't really been that long since my last group exploit. Katie's eyes went wide, and a smile crept across her pale face.

"Did you like it?"

"It was fun," I answered.

"Would you do it with me?" As nervous as I was and how poorly I had been handling a proposition that I hadn't imagined going very smoothly in my head to begin with, my heart sparked with excitement as my lustful desire began to look like a real possibility. It felt like a dream. I couldn't believe that after desperately trying to find the smoothest way possible to ask Katie to participate in group sex, she was now essentially doing the asking instead.

"If you think you could get one of your boyfriends to sandwich you," I said with renewed confidence, "then I'm in." I took a sip of wine to keep myself from saying anything else at this point.

"One of them?" she responded. "I bet I could get both of them and really make it a party." Damn it, I shouldn't have taken that drink, since I immediately choked a little on the wine as those words came out of my friend's mouth. Katie simply finished her glass as I sputtered on the alcohol for a bit. Now she was laughing a little as I recovered just enough to simply stare back at Katie. It's a good thing Katie and I were close friends, because I had made quite a fool of myself. At that point, though, I just couldn't help but think that my aforementioned anonymous acquaintance had practically spoken into being the best possible scenario!

Later that night, I took Katie back to my place and nailed the hell out of her for the first time in months. It was immensely satisfying to rock Katie hard in my bed, especially after she had agreed to fulfill such a dirty desire of mine. A couple days later, we banged again, and this time she let me use a dildo in her ass for a little bit and then actually briefly put my cock in there in preparation for the gangbang. In fact, it was the first time I had had strictly anal sex with a girl outside of group sex and only the second girl total that allowed me to put it in her butt. I was encouraged by how well she took the pounding in her shitter that night, even if it was short-lived, and I praised her for it.

"This isn't my first time," she said as my balls were getting ready to burst, my hips slapping against her ass cheeks as my cock dove deep into her dark hole over and over again.

"I didn't know that," I said, straining as I held off my orgasm for just a moment longer. "Why did I have to wait this long?"

"You never asked!" she replied. Fair enough, I thought, just as I unloaded my seed deep in her ass. I couldn't believe what I had been missing out on before I hooked up with Katie. During all these years of friendship, I would have never guessed she would ever let me do any of these things to her.

Within a week of the anal sex, we had our next event planned. It all flew by faster than I could really comprehend it. Before I knew it, I was gripped with nerves on that chilly November evening as Katie went into her kitchen to fetch some drinks for us and for our company that had yet to arrive. Katie swore it was her first time doing anything like what we had planned, but to this day I still suspect she was lying, especially given that she had so eagerly agreed to it this time. I must say, though, that her anxiety was clearly evident this night, supporting her claim of inexperience in this realm. I, on the same token, was a bit anxious myself. Even though it wasn't my first rodeo, it was the first such experience with a new girl, bringing a whole new set of uncertainties night.

By the time Katie and I were finishing off that first drink, the second lover arrived. His name was Keith, a guy taller and bigger than I, built pretty well and with dirty blond hair. I've never been comfortable meeting new people, so being introduced to someone who was soon going to be naked and fucking the same girl with me was truly awkward for me. Fortunately, that moment didn't last too long, as Katie's other friend, Dan, showed up just a few minutes later, which meant we could get started soon. Dan was shorter than I and about as skinny but had darker skin and hair.

At this point, it would be appropriate to describe what Katie was wearing. For starters, she wore a low-cut white shirt that revealed some of her cleavage, of which she had plenty, seeing how big her boobs are. In addition, she sported a pink skirt that went two-thirds of the way down her thighs and black boots that came just below her knees. The boots had high heels on them and were being worn specifically because of the fantasy I had described to Katie, wherein she had worn such boots. As for the rest of her appearance, her blonde hair was curled and hung down just past her chin, her bright blue eyes shined past her dark eye liner and her rosy, pale face glowed with makeup that covered her light freckles.

After a brief moment of uncomfortable silence, Katie offered drinks to anyone who wanted one. Both Dan and Keith accepted the offer, reminding me of my first experience with group sex where I imbibed above my normal consumption of alcohol. Katie, however, was quickly getting pretty tipsy, naturally. As much as I'd kind of disapproved of her tendency toward alcohol in the past, I was surely thankful for it now.

We didn't loiter for long, as we were all on the same page as far as moving on with the festivities. Keith was the one to say what we other two boys were thinking by suggesting we head into the bedroom. It wasn't my first time getting the invite into Katie's room, but never before had I had to follow behind two other guys, who remained silent along with me as we departed from the living room. I'd never actually met either of these guys, despite the fact that Katie had been fucking them for at least the past couple years, though I didn't know at what consistency.

Katie held the door open for her three guests and then closed it tightly behind us. I think all three of us guys were magnetized to her beaming grin and her white flesh glowing in the well-lit room. The decor of stuffed animals, band posters and the Walking Dead paraphernalia didn't comprise exactly the backdrop one would expect for this type of sexual activity, but it aided my excitement in a way. After all, this episode wasn't porn. It was the real thing.

In my experience with Katie, she had never been the type to put on a striptease or much foreplay, and the increase of potential discomfort this time only encouraged her all the more to keep it moving, I imagine. She simply headed straight to her bed and was tossing aside clothing before she'd even gotten comfortable. When the shirt came off, we three men cheered her on and cheered even louder when she removed her bra. I wish I could describe Katie's stripping in more detail, but everything was such a whirlwind, I can't even honestly say I remember much more about Katie's undressing that night. Before I knew it, Katie was wearing nothing but her boots, and the eyes of three men were transfixed on her big bare breasts.

The moments following Katie's stripping flew by no slower. Before I knew it, I was naked along with two other guys, all of us hard as steel and ready to get to work. The discomfort with being naked around other guys was something that had dissipated after just one or two runs with group sex, and knowing full well what was ahead eliminated any hesitation for me while remaining firm in my own sexuality. I didn't pay enough attention to my new comrades to tell how anxious they were. I didn't care, anyway. I just needed someone to help me give this girl the fucking she needed.

Since Katie had an intense night ahead of her, we all agreed to start one-on-one to break her in. Keith went first, standing at the side of the bed while Dan and I watched Katie lie on her back and hang her legs over the edge of the bed, spreading them and allowing Keith to step up right between them. Katie leaned forward, her knees on either side of Keith's waist as she held her head up and helped Keith push his rock-hard cock into her pussy. In retrospect, it would have been polite to at least get Katie warmed up first, but we were all so eager to get going that Keith went straight in.

For the next several minutes, I watched on silently with a perfect stranger as I watched another unfamiliar man in front of me have his way with my good friend. Katie clutched the comforter beneath her with both hands as her legs curled around the hips of one of her three lovers while he held Katie's hips and pounded her pussy furiously. Having no real romantic attachment to Katie, I felt no feelings of jealously arise; instead, it was actually really hot to watch the young blonde get nailed by another dude.

Katie moaned and cried out, occasionally spouting some profanity. Dan and I hardly uttered a sound but just stroked ourselves as we watched the spectacle before us. The only sounds coming from Keith were his grunting and the steady slap of his hips against Katie as he rammed his cock into her pussy over and over again, rocking Katie back each time he thrust into her, which caused those terrific tits to bounce wildly in rhythm with his motion.

Once Keith was sufficiently worked up in his own estimation, he pulled out and stepped aside. Katie immediately looked at me and beckoned me over, remaining on her back and lifting her boots up into the air, spreading her legs wide. I stepped up to take my place, all but forgetting the presence of the two onlookers. Following a brief glance into the pale girl's sparkling blue eyes, I peered at her glistening open pink twat and guided my cock into it with one hand. It slipped easily inside my friend, who immediately lowered her ankles onto my shoulders.

Katie and I moaned in unison as I sank all the way inside her tight, wet pussy, my balls resting against her taint. She was already set to go, thanks to Keith's work on her, so I was able to immediately retract my cock and slam it right back into her, causing my balls to slap hard against her. From there, I just thrust in and out of her, hard and fast while she moaned, again clutching the blanket on either side of her.

I started with holding onto Katie's hips as I fucked her, but Katie's supple breasts eventually drew me in. I leaned forward and latched onto her boobs, still thrusting powerfully into her young body while her boots were forced higher into the air as they rested on my shoulders. Meanwhile, my two new friends watched on as our shared lover was nailed right in front of them.

I leaned closer and closer into Katie for several more minutes, my face coming near hers as she moaned and laughed in response to all the attention she was getting. Her legs ended up slipping down my arms and resting in my elbows as I practically folded her up from drilling her. I banged her hard and fast until my cock was just short of exploding, and then I stopped, trying hard to hold off an orgasm, which I managed to do successfully before pulling out, getting her pretty close to her own climax, I think.

Katie sighed as I exited her, and Dan was right there as soon as I walked away. He got Katie on her hands and knees and, like the other two of us, stood on the floor at the edge of the bed and slipped his cock into the girl's pussy. For the next few minutes, Keith and I watched with lust as our mutual friend was railed hard for the third straight time, her hair and boobs shaking, her body rocking as she was fucked from behind.

Dan held tightly to Katie's hips and gave her a stiff pounding for another moment before slowing down and pulling out. Once he stepped away, Katie's fate was up in the air, as no one knew exactly what to say or what move to make next. Being the one who suggested this raunchy idea in the first place, I took the initiative to join Katie in the bed and get on with what we were all here to do.

A few words were spoken, and then we were all eager to get going. Katie was trembling a bit, betraying her nerves as she prepared for her first double penetration. I didn't get a good read on the guys, whether they were anxious or not, not that I cared. I, of course, was beyond excited to get going. I think my cock got even harder as I lay down on my back and mentally prepared myself to have some debauched fun with my blonde friend, who at that moment was climbing on top of me in order to take me into one of her three holes that would all be full in just a few more moments.