Best Laid Plans

Deep down, I knew that a guy like Jake would never be satisfied with just a blowjob, even if he came. But I had been unwilling to think about what now seemed like an inevitability, giving my anal virginity over to my hunk of a roommate. However, as the painfully swollen cock trapped underneath my panties reminded me, I was still desperately horny. The combination of having gone so long without sexual contact and having given up crossdressing meant that I now couldn't control my lizard brain. I gave him a silly smile.

In response, Jake leaned over and picked me up off the floor like I weighed nothing, and I looped my arms around his muscular neck as he princess-carried me to his room. While I wasn't particularly heavy, I was shocked at the way he manhandled me like a child, and I was reminded once again of the vast gap in our bodies. We were both technically guys, and yet the differences between us were like those between an Alaskan Malamute and a Chihuahua. Was I really expected to compete with this Herculean specimen for female attention?

I surrendered to the realization that it had been futile all along, that this was where I was destined to end up, sooner or later. At that cathartic epiphany, I shuddered as a weak stream of semen pooled in my panties. Gently lowering me onto his bed, Jake opened his nightstand drawer to produce a bottle of lube and a condom.

"What are you doing, silly?" I giggled. "I can't get pregnant."

He grinned, and tossed the condom aside as he squeezed a generous amount of lube on his still-erect cock. I expectantly got on all fours, arched my back, and presented my ass to him. I could only imagine the erotic view he was getting of my short dress riding up my hips, garter straps exposed, and small wisp of black lace covering my puckered, hairless hole. I could feel my cum from earlier dripping down my thighs.

"Somebody's wet," my roommate said as he slapped my ass, and I yelped girlishly. I felt him slip my thong to one side as cold, slimy lube first drizzled onto my asshole, and then made its way inside me as one, then two fingers began warming me up. Unsurprisingly, he was no novice at anal.

I was no stranger to anal masturbation, but it was an entirely novel sensation to have another human being play with my ass, especially one as attractive and experienced as Jake. Soon, he was stroking the inside of my hole with three fingers, and I knew it was time.

"I'm ready," I whispered.

Surprising me, Jake flipped me onto my back, and, grabbing my heels, spread my legs apart.

"I want you to see me fuck you, Jennie," he growled. "I want you to watch as my cock slides inside you."

I nodded eagerly as Jake positioned his hips and brought his engorged cock to my eager and waiting ass. I gasped when he began pressing the spongy mushroom head of his manhood into me, but with surprisingly little resistance, it slipped inside me with a soft pop. For the first time, I had a real cock inside me, and it was none other than my roommate's.

"Your ass is so fucking tight," he grunted, as he slowly began thrusting. All I could do was moan wordlessly with feminine pleasure. With his grip on my stilettos, I realized how he was in complete control of my body, but this vulnerability, far from alarming me, only further increased my arousal.

As Jake increased the speed and depth of his thrusts, I realized that when I had been masturbating to Jake and Rachel fucking, it wasn't because I wanted to fuck Rachel. I wanted to be Rachel: desirable, sexual, and both pleasing and being pleasured by a real man. Now, impaled on my roommate's massive cock, my subconscious fantasy became a reality.

With each thrust, I was unconsciously matching Jake's animalistic grunts with girlish moaning of my own. With each thrust, I felt the final vestiges of my masculinity being fucked out of me. The impossibly full feeling of being penetrated by my roommate, along with sight of his chiseled body, dripping with sweat, put my brain on autopilot. I was now acting solely on primal, sexual, instinct, as I squirmed and bucked my hips in time with his, trying to hit that elusive "p-spot."

Abruptly, I gasped when the combination of depth and angle aligned just right, and Jake's cock began ramming my prostate. He sensed my pleasure and redoubled his efforts, causing me to grab his muscular, iron-hard forearms with my hands. My nails dug into his skin as I writhed in pleasure, but he didn't seem to mind. Instead, his cocky grin turned feral as he brought me closer and closer to orgasm.

"Are you going to cum for me, Jennie?" he growled. "Cum like a good little slut while daddy breeds you."

In the back of my mind, I knew that I shouldn't be able to cum while my small "clit," still safely nestled in my panties, was still barely engorged. But the fuzzy, persistent warmth that was spreading outwards from deep inside my ass was suggesting otherwise. I watched intently as my ass seemed to swallow up, then disgorge, Jake's thick meat.

"Please don't stop," I panted. "I'm so close, I'm so close, I'msoclose, I'msocl-"

Jake's cock pulsed and swelled inside me, releasing its second torrent of molten seed that day, the knowledge that I had been the one that had brought him such pleasure took me over the edge as well. Waves of liquid euphoria poured over me and I screamed as I came.

As Jake and I continued to ride out our respective orgasms, each motion sent immense ripples of pleasure radiating out from my abused hole. Individually, they dwarfed even my most memorable orgasms up until that point, and in the aggregate, well...there was no going back. I was well and truly Jake's girl.

Finally, after what seemed like an eternity, Jake released my heels and collapsed on top of me. I wrapped my legs around his waist to keep his manhood lodged deep inside of me, and clenched my sphincter to massage his slowly softening cock. He groaned in pleasure, and kissed my neck in response. The unfamiliar sensation caused me to shiver delightfully.

"You're even hotter than I remembered," he mumbled into my collarbone. "And you fuck better than I had hoped."

My jaw dropped in shock. So he hadn't blacked out that night he caught me. Then why didn't he say anything? Was all of this truly a fateful coincidence or merely an elaborate ploy that I had fallen for?

I was about to speak, then closed my mouth and smiled contentedly. It didn't matter, did it? We had both gotten what we had deeply desired. As for how this would change our relationship going forward, well, who knew when the world would return to normal? Until then, I had plenty of sexy outfits to try out. And more importantly, I thought, smiling to myself, I had Jake all to myself.

Jennie's note: Returning to "feature length" stories! Please leave a comment, as it encourages me to keep writing!