A Thorn in the Rosebud

My legs were shaking, my lips quivering. Charlie, a man twice my age, was between my legs. His fingers dancing around my wet slit. He pulled my lips apart, exposing my small, hard clitoris. His tongue ran up and down, finally settling on my clit. My hands were on his head, gently guiding his mouth over my sweet spots. All of a sudden, he rose up a bit.

Confused, I asked "What's wrong Daddy?"

"I want to try something, just relax."

He ordered, with a quite stern tone in his deep voice.

I laid back and closed my eyes. A tad nervous about what he would do next. He raised my legs a bit and bent back down. Suddenly and surprisingly, he was licking my asshole. I had never felt something like that before. It felt odd, but strangely satisfying. He continued to lick my virgin asshole and I let out soft moans into the pillow.

His tongue, wet and slippery, started to dart in and out. I could feel the juices from my pussy flowing out. My hard clit was throbbing and I felt light headed. He stopped. I opened my eyes. He could see a slight disappointment in my eyes. All he did was smile and rub my thigh.

"Do you like that, sweetie?" He questioned.

"Oh my god it's amazing!" I exclaimed breathlessly.

"Would you like to try going a bit further?"

I paused for a moment, he knew I had never done anything sexual back there. We had talked about it in our many late night conversations. It always seemed so far off, like it would never happen. I had seen many porn videos with anal. The woman always looked like she was having a decent time. Maybe it would feel nice, maybe it wouldn't hurt as badly as my friends told me.

"As long as you're extremely gentle, and stop if I say so." I said nervously and unsure of my decision.

"I will be very gentle, baby. But I will not stop until I cum." He stated with little emotion.

Thoughts began to swirl around my head. What if it's the worst pain imaginable? What if I'll never be able to sit down again?! I began to feel a knot in my stomach. My hand trembled as Charlie took it in his, seeing how obviously nervous I was.

"Don't worry Cait, I'll make sure you enjoy it as much as I will." He assured me with a tender smile coming across his face.

"Alright, I guess we can try it." I expressed.

I laid on my back with my legs spread wide. Still holding Charlie's hand. I always liked his hands. They were big and manly, but extremely soft to the touch. Just the kind of hands a young woman like me would need to guide her through this new experience.

Charlie positioned himself so that his fingers could explore my uncharted territory with ease.

I breathed deeply in anticipation. He took his index finger and traced my puckered asshole. It tickled a bit, so I didn't mind it. It seemed to go on forever, until finally, he put the tip of his finger inside me. I thought to myself that it wasn't so bad. Maybe it won't be as bad as I thought it would be. Charlie kept it there for a moment, then started moving it around. I felt a sort of burning sensation, but didn't say anything. I kept breathing and watched the clock on the bedside table, watching second after second drag by. Then, without warning, two fingers. I closed my eyes tight. Instead of telling him to stop, because I know he wouldn't, I reached between my legs.

Shockingly, I was wet. I inserted a finger of my own into my cunt. The mix of pleasure and uncomfortableness was actually quite thrilling.

Charlie pulled his fingers out gently and leaned down to kiss me. As our lips touched, I realized that he does care about my own pleasure, and that this new experience would be okay. We broke the kiss.

"Lay on your stomach, sweetie." He softly purred into my ear.

I complied, putting a pillow under my stomach, so my ass was raised. He got a bottle of lube from the nightstand and coated the outside of my asshole with it. Then put some on his cock. All 8 inches glistened. He aligned himself and mounted me. With one hand he spread my cheeks, with the other he guided the tip of his cock into me. It didn't hurt per se. Thank God for lube! Inch by inch, he worked his way into my asshole. When he got half way in, he stopped.

"How are you feeling?" He inquired sweetly.

"I'm okay, just remember to be gentle please." I stammered.

"I will."

After a few moments of non-movement, he began to slowly go back and forth, causing his hard cock to go in and out of me. He picked up speed. Now going a little faster, a noticed a rush of warmth under me. My pussy juices were flowing like a waterfall. I was actually enjoying myself!

I laid motionless, but told him he could go faster if he liked. He did. It started to feel pretty good, the lube was definitely a good idea! Charlie started going faster and harder. With each thrust I moaned. I was always very vocal during sex, but never like this. I couldn't stop moaning and purring. He lowered himself and kissed my back. I felt a shiver. It was so wonderful. I was in a state of pure unadulterated bliss!

"You like this, baby?" Charlie asked.

"Oh fuck yes!! Keep going please!" I answered, almost out of breath.

Charlie started pumping faster and faster. I could feel his huge cock starting to throb. His cock was all the way in my newly broken in asshole. My clit was so hard, aching to be touched. I reached down and started to rub furiously. Within minutes, I was cumming. My body started to quiver and convulse.

"Please baby, cum in my ass!" I screamed between moans as I climaxed.

"I'm gonna cum baby, deep in your asshole!"

All of a sudden, he groaned, he thrusted hard several times. Finally, Charlie collapsed onto me. I've always enjoyed feeling the weight of a man on top of me. We laid there for a few moments while his cock got soft inside me. Finally, he got up and laid next to me, gently rubbing my back. His kissed my forehead in such a tender way. We smiled at each other for the longest time. I was finally conquered, in every way I could think of. I couldn't wait to do it again!