If any other of my female friends were to fulfill my dirty fantasies, I knew Katie would be my best shot. Even though the young blond wasn't really my type, 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.
After a couple years of platonic friendship, I started to see Katie in a different light. The more I trusted her as a friend, the more attractive I found her rosy cheeks, pale skin and thicker frame. After a long run of sleeping with petite brunettes pretty exclusively, I saw my relationship with Katie evolve, culminating in hot, no-strings-attached sex one fateful night.
It was almost immediately after our first fuck that my depraved mind envisioned Katie as the center of attention for multiple men. Before long, I found out that she was currently banging a couple other dudes and was kind of a slut, actually. 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 multiple sex partners 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 had Katie right where I wanted her.
Nerves gripped me this chilly evening in late November as Katie went into her kitchen to fetch some drinks for us and for our company that had yet to arrive. It was almost two years since my first dive into group sex, making it only appropriate, then, that Katie and I were waiting for her two other lovers to show up. I really had suspected that Katie already had experience with multiple partners, since she had so eagerly agreed to it this time, but she swore it was her first time. I must say, though, that her anxiety was clearly evident this night, supporting her claim. I, on the same token, was a bit anxious myself. Even though I'd participated in group sex before and loved it, trying it with a new girl brought a new set of uncertainties.
It had taken a long time to build up the nerve to tell my fantasy to Katie, and as she emerged from the kitchen with two full wine glasses, both of which shook in her hands as she came to join me on the couch, I thought back to the last time I'd had a drink with Katie, which was two weeks ago when I finally shared my shameful desire with my friend. That night started innocently enough, as just two friends' grabbing a bite to eat and some drinks. It was, admittedly, a little out of the ordinary for me though, since I'd hardly ever drink and never would have suggested alcohol as a fun option for an evening under normal circumstances. However, Katie clearly had a tendency toward alcohol, a weakness of which I intended to unapologetically take advantage.
Being a classic over-thinker, I planned out that evening 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. 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 high risk for the situation to be awkwardly overheard. Like I said, classic over-thinker.
We had a lovely night, and 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 two years ago, we'd had sex only six or seven times. 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, 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 don't know but is 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," 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.
