Sexual Crossroads

Back when my youthful horniness was at its peak, I found myself at a crossroads with my sexuality. I had only hooked up with girls, however, I often caught myself fighting off feelings of sexual excitement at the thought of my best friend, Ryan.

While I considered myself to be straight, I felt moments of weakness in the locker room after soccer practice. Although we would never get fully naked in front of each other, Ryan and I would strip down to our boxers to change from our gym shorts into our street clothes, and vice versa. On several occasions, I couldn’t help but notice that Ryan’s boxers fit loosely over his skinny legs. When we were sitting, if I looked at just the right angle, I could sometimes catch a nonchalant glimpse of Ryan’s compact ball-sack as he lifted one leg into his jeans, and then the other.

In these moments, I would feel strong urges of longing. I would envision taking Ryan’s cock into my hand, and letting it grow firm and hot in my closed palm. In my guilty fantasies, I would put the base of Ryan’s cock against my face, feeling the warmth of it on my cheek. Finally, I would lick his throbbing manhood from the base of his shaft, slowly up to the tip of his dick’s swollen head.

Convinced that these idle daydreams would remain just that, one day Ryan called me out of the blue to ask if I would take his sister, Beth, to a mixer at her community college.

“She doesn’t have a date,” he stated. “If you took her to the dance, we could hang out later back at my place and throw back some adult beverages.”

I had absolutely no interest in taking Ryan’s socially inept sister to this mixer, but I said I would, frankly, because I couldn’t think of an excuse fast enough.

As anticipated, the mixer was awkward and boring. We left the dance at around 11, but since Beth wasn’t particularly popular, we went straight home rather than hitting the after-party scene.

Ryan had already started drinking by the time I arrived back at his place. Claiming exhaustion, Beth went off to her bedroom, leaving Ryan and me to our own devices.

“I’m drinking screw-drivers… Want One?”

I greedily accepted Ryan’s offer and, after several drinks, we decided to take the vodka and OJ up to Ryan’s room.

Sitting on Ryan’s bed drinking, I noticed something I’m not sure I was supposed to.

“Is that a naked dude on the cover of that magazine?” I exclaimed, noticing a glossy photo of a half naked man. The magazine was partially hidden under Ryan’s bed.

“Oh shitt, yeah…” Ryan stuttered, trying to find the right words. “I’m not really ashamed of it, man. I guess… I guess sometimes, I just feel like looking at pictures of guys.”

Silence enclosed the room like a blanket. I felt my heart pounding against my rib cage. Wanting to admit that I felt the same way, but not brave enough to take this step, I instead said nothing.

Eventually, I broke the silence: “Yeah…Don’t be ashamed about it. To be honest, I feel the exact same way. I don’t really want to kiss a guy or have sex with a dude, but sometimes I do picture jerking off with a guy, or even maybe giving a guy head or something.”

I couldn’t believe my ears. I had admitted it. My deepest secret verbalized for the first time. I felt naked, exhilarated, and excited all at once. There, sitting on Ryan’s bed, drinking screw-drivers in the dark, we realized that we shared a similar burning curiosity.

Then, the unthinkable happened. Ryan leaned over. Slowly, I felt his lips brush against mine.

I could taste the sourness of the OJ and vodka as Ryan brought his lips to my own. I opened my lips with hesitation and let Ryan move his tongue against mine. I felt lightheaded and trembled as blood rushed out of my head and swelled hard against the fly of my jeans. Ryan and I began unbuttoning and unzipping each other’s pants at the same time. I would finally get to feel Ryan’s dick enclosed in my hand’s caressing palm.

Already firm and eager, Ryan’s cock felt smoother and warmer than I had even imagined in my fantasies. Finally letting months of pent up sexual tension wash over us, Ryan and I stroked each other’s cocks with zeal and exuberance. I felt the weight of Ryan’s pelvis grind into mine as he got on top of me and whispered in my ear: “God, you’re so fucking hard right now.”

I allowed myself to surrender to the moment as Ryan parted my legs and began to circle the tip of his pointer finger around the sensitive rim of my virgin asshole.

Ryan gently pushed the top of his pointer finger into my ass, slowly opening tight, tender muscles that had never experienced the sensation of another person’s touch. In that moment, I decided, if Ryan wanted to put his cock inside of me, I could never bring myself to say “no.”

Ryan spoke not a word, but instead playfully teased the rim of my asshole with curious fingers. A deep yearning for more burned inside me, but I was too ashamed to verbalize my desires. I tried to stay strong and wait for Ryan to make the next move, but my patience was growing thin with increasing lust.

At last, Ryan spoke up.

“I want more.”

I looked up at Ryan and gave a shy nod of agreement. I was ready and willing to submit to the feeling of his full, eager manhood. I felt a little ashamed to admit that I was fervently anticipating the moment of insertion.

Ryan had stopped teasing the rim of my asshole, and had moved his pointer finger deep inside, opening my hole. First one finger, then two, I felt a flush of euphoria as Ryan brushed against my g-spot.

Ryan’s lubed dick glistened in the darkness as he lowered himself into me. First, lightly pressing the tip of his dick at the opening of my asshole, then, easing his dick’s swollen head through the resistant grip of my hole. I felt all my muscles tighten over the fullness of Ryan’s cock. The tip of his dick nudged my g-spot with a determination that drove me into a state of ecstasy.

Ryan established an aggressive grip on my cock and started stroking and thrusting with intense abandon. I felt myself let go of all inhibition, and climbed on top of Ryan, riding his cock with confident thrusts. Looking down, I saw my hard dick bobbing in the air. Putting my left hand down on the bed for support, I furiously jerked off my own cock as Ryan moved deeper and deeper into my ass, rubbing my ever-growing g-spot.

Knowing I could only stand this for mere seconds before submitting to a violent climax, I whispered, “Fuck, Ryan…You’re gonna make me cum.”

Almost embarrassed by my lack of stamina, I came in hard, steady waves of hot, thick semen.

“Sorry, man… I couldn’t hold out any longer,” I whispered. Defeated, yet satisfied.

A sheepish smirk developed on the corners of Ryan’s mouth as he replied…

“Don’t sweat it Skip… I just came too…”