I woke up about two hours later, feeling Jake's hand roaming over my hairless body. I could also feel a very hard cock poking my uncovered ass. Jake was licking my ear. What a way to wake up! I yawned and stretched.
"The sleeping beauty awakens from her slumber!" Jake exclaimed, "You worked hard earlier and deserved that sleep but there is more to do."
I wondered if he was going to make me suck him off again. I was excited about the prospect but he made no indication that he wanted to use my mouth again. Instead, his hands just kept gently stroking me and cupping my naked ass cheeks. I could get used to this; I thought as I felt my balls getting sticky from the precum leaking out of my locked cock. I also felt his now fully engorged cock poking my ass.
I was disappointed when Jake got up and out of bed. I had been enjoying his hands and warmth so much. He went to his pants and got a bottle of lube out of the pocket.
"I have been dreaming of popping your tight ass for over two months now." He stated, mischievously.
This was a shock to me. I had never thought of being fucked in the ass before and I shuddered in fear.
"Don't worry Sweetheart." Jake said, soothingly. "I know it's your first time, and promise to go slow."
I was scared and excited beyond belief. I had been dressing and acting like a woman, these past few months. Now I was going to get fucked like one.
Jake climbed back onto the bed and leaned back against the tall headboard. He motioned for me to sit on his lap. I did so, straddling his torso with my bent knees on either side of him. He wrapped a strong arm around my waist and pulled me in for a juicy kiss. In this position my pantyless ass was jutting out and framed between the corset, stocking tops and garter straps. Jake started gently stroking my ass as we made out. It felt so hot. He made sure to run his fingers through my crack gently brushing across my pucker.
Jake opened the top on the bottle of lube and poured a small amount on his large finger. I watched in trepidation, and felt his hard cock poke my thigh. He ran this lubed finger up my crack applying more pressure. It felt great and I pushed my ass out some to try to get more pressure from his finger. Jake poured a little more lube onto his finger. He started gently applying pressure to my pucker, in small circular motions with the pad of his finger.
I couldn't believe how erotic it felt, and moaned into his lips, that were still kissing me. Soon, the finger ever so gently started working its way into my hole. I did not like the feel of his sharp nail, but the shame of knowing that my body was being invaded more than made up for this discomfort. My stomach was a mess of emotions, mostly humiliation and fear of what I was to become. By now the finger nail worked past my tight opening and I felt the divine pleasure of my sphincter clamping around his big finger. As he slowly worked it in and out with small thrusts, the friction it made was the most arousing feeling that I ever had. I tried pushing my ass out even farther to get more of his finger in but felt his other fingers on my cheek. It would not go in any farther.
We made out for a few minutes, with Jake's finger slowly going in and out of my hole. Not only was I sucking on Jake's mouth like a whore, I was wiggling my bottom like a slut.
I moaned onto Jake's tongue in despair, when he removed his invading finger.
"Take it easy Baby." He soothed, "It's only the beginning."
He poured more lube on two of his fingers this time. I was worried but my hole welcomed the return of his finger. Only this time, once the finger was all the way in, I felt the hard nail of a second finger. My midsection shuddered, in its tightly bound corset. The discomfort of the hard nail was brief as it too inched its way into my bowels. I could feel my asshole stretching around those two burly digits. The stretching hurt in a good way, for just a little bit, before that divine friction took over once more.
