by Kis Lee
(02/20/08)
He kneeled between my legs with his cock in one hand and a bottle of lube in the other. It was his first time trying anal, and it was my first time trying it with him. I kept telling him to relax, but the look of determination on his face was almost funny.
"Now what?" he asked as he stroked his hard-on.
"You're too thick, honey. We can't go immediately from cock to ass. It doesn't work that way."
He placed the lube back on the nightstand. "Well, tell me what to do."
I hooked one leg around his waist and brought him closer. "Get me off again. I need you to relax, and I need you to help me relax."
He slid forward, his lips landing on my clit. His chin pressed against my pussy, and I shivered at the way his stubble felt. His tongue circled my clit slowly as his dark eyes stared up at me.
I sighed and said, "Do that thing you do."
He sucked my clit into his mouth and slid two fingers inside me at the same time. His fingers curled upward, then inward, pressed hard against a certain spot. I bucked against his face, but his chin kept me in place. His mouth played with my sensitive clit, sucking on it, pressing against it with his tongue, strumming it with his lips. His fingers fucked me hard until I was grinding against his chin. He alternated between fast strokes and deep, sensual strokes.
Rocking my hips, I spread my arousal all over his chin. He paused to clean me up with his tongue and then sat back on his heels. "Are you relaxed enough?"
I looked at him through half-closed lids. "Why don't you check for yourself?"
The bottle of lube appeared by his side, almost like magic. A solitary drop gelled on his fingertip and dipped below my line of sight. His two fingers returned inside me, spreading me from the inside. His lubed fingertip circled my asshole slowly, prodding, pausing. It was a hesitant finger, unsure of itself.
I spread my legs wider and told him, "Relax."
He exhaled loudly. At the same time, the tip of his finger pressed against me. I exhaled loudly. His finger dipped inside me, finally entering me. We both sighed.
"Relax."
The fingers in my pussy moved at glacial speed as the finger in my ass pressed forward. I coaxed my body to relax as he finger-fucked my ass. I rocked against him until he found a comfortable rhythm. With a tilt of my hips, I let his fingers slide out of my pussy. His other finger stayed in place, resting, waiting for my next move.
I played with my clit as he explored my other hole. His finger eased in and out in incremental movements as I willed myself to relax even further. His finger became bolder with another dab of lube. I looked up at him and his eyes showed wonder. Then confusion as to what he should do next. The unspoken question in the air: "Can I? Now?"
I answered the hidden question by grabbing the condom hiding beneath my pillow. His finger never left me as I rolled the condom onto his thick cock. I still thought his cock was too thick, but I was willing to try. I had to at least let him try.
The pillow underneath my back added a few inches of height. I touched his wrist and his finger slid out of me. He scooted closer to me until the tip of his cock pressed against me.
"Relax," we both said at the same time. Then we laughed. Paused. And then we laughed again. I told him to take the lead and tried to breathe normally. I let the tension drop into the mattress and relaxed.
He was generous with the lube, and the extra droplets felt cold against my asshole. He warmed with his fingertips and then rubbed the rest over his cock. His fingertip returned to its destination spot and massaged me in sensuous circles.
"Are you relaxed enough?"
"Yes."
"Do you need me to get you off again? More lube?"
I smiled at him. "Quit stalling."
His fingers stopped what they were doing. The tip of his cock felt hard and big, perhaps too big. I told him and that seemed to turn him on even more. I coaxed him with my moans and his cock pressed harder. The lube made him slide close to my pussy and we both giggled at the change of direction. He gripped his cock and pressed forward. I felt that moment of resistance. That feeling that it wasn't going to happen. That his cock was too big and we would have to try another time.
The moment passed, and we both felt his cock pop inside me. I heard a surprised "Oh!" but I wasn't sure if it was him or me. It was just the tip but the sensation was almost overwhelming. A split second later he slipped out of me. He pressed forward again and the moment of resistance was shorter. It was a slow, methodical process with several pauses and repeated applications of lube. If it sounds scientific, that's because it was. That's one thing that you don't read about in anal erotica. They make it sound so quick and so easy, like a cock just slides into an asshole. They don't take into account the meticulous determination that you need for it to work.
We were both meticulous and determined. It took a while for half of his cock to fit inside me. The lube got messy so we grabbed his thickest towel. Soon we established a slow dance of his cock sliding in and out of my ass. It wasn't the same as him fucking me, but his strokes kept a steady beat.
His hips lost their hesitation and he fucked me hard and slow. I rubbed my clit in a faster rhythm and became lost in my orgasm. My squirms made him move slightly faster and we didn't even try to maintain the same beat. I danced to hard techno and he moved to a slow R & B jam. I came hard and he shuddered against me a few seconds later.
"Did you come?"
He barely gasped that he did. I didn't mention that I was too preoccupied to notice.
I pulled his body against mine and squeezed my legs around him. "Did you enjoy your first time? I mean, our first time?"
The smile on his face was enough of an answer.
