At a recent holiday party our eyes met. Strangers at first, but it ended well beyond that. At first just two men glancing innocently. Then another glance. Then a few more glances with subsequent stares. Now it was a game of obsession to see who could catch the other looking. Finally I walked up to him, brave from a few glasses of wine and holiday cheer. Brave to not only approach this handsome stranger in his late 20s, but also to finally act on my innermost desires to be with another man. Or at least try. Who would know if it would bomb.
I said "Hi, I'm Jamie" and his corresponding smile told me he was down with every single thought inside my head. He greeted me back, introducing himself as Kyle with his words, but truly welcoming me and telling me all I needed to know with the attendant grab of my hand. A grab that lingered, and lingered, with a tight squeeze. Small talk ensued for 15-20 minutes, smiles and flirting exchanged. My heart racing, my first act on pent up impulses. But how far would it go? You see for years I have fantasized about giving head. I crave the tip of a shiny penis, I crave the taste of precum, I cannot get enough of the thought of being his dirty little slut and letting him fuck my mouth as he sees fit. All while donning women's attire, whether it be full blown slutwear, or even just some hose and heels to make me feel feminine. I was focused on pleasing him, and taking his cock in my mouth. Prior to that night a few weeks ago, "he" was unknown, yet at the same time was everyone. But here a real opportunity presented itself and I was ready to act. Tucked away in my car I had my emergency kit of size 11 heels, thigh highs, panty hose, and a skirt. Would I get the chance tonight?
After the small talk, I excused myself from Kyle for a minute and told him I had to grab something out of the car. He looked nervous, wondering if I was peeling off the encounter. Nothing could have been further from my mind. I assured him I would be back and when his blue eyes lit up with a smile, I knew he would wait. I grabbed my backpack out of the trunk and returned to the house party inside, which was starting to thin out as it neared midnight and people hit their limit. I grabbed Kyle's hand and announced I was back, his smile was like a hug. And I noticed in a few seconds a growing bulge in his dress pants. It was hard for him to hide it both because he was swollen beyond belief, but also because of the fact that he had 9 inches tucked in there and that cannot be constrained by many pants, let alone tight ones.