Chapter 2

I knew from experience that fourteen year old young ladies can be skittish about penetration into one's anus. I was experienced performing anal sex with at least twenty different women who were sixteen or younger. My repertoire included one woman who turned thirteen years only seventeen days before I received the pleasure of merging my cock into her ass. She actually was one of my more enjoyable experiences because she enjoyed it so much herself. From my extensive firsthand knowledge, I knew girls were frequently unnecessarily nervous which contributed, especially upon initial entry, to an experience that was less than it should be. Of course, my extra fat cock contributed to a misconception of pain, when it was actually pleasure inducing.

I walked over to Charlotte. She idly rubbed her tits in the afterglow of her coupling with Bones. A steady drip of Bones' cum and her own juices exited her quim.

"Turn on to your stomach, Charlotte," said I, "I'll give you a rub down to release any tensions from your experience this day."

"I think Mr. Bones took care of my tensions," replied Charlotte.

"I am a doctor," said I in an official manner, "I can see tensions in your body. Please turn over."

"Okay, Doctor," said Charlotte, in proper respect of my authority.

I climbed up on top of the table with my legs straddled over her body. I rubbed and massaged her back. As Charlotte became used to my gentle touch, her body relaxed and melted into the table. I took a long extended time to put her at ease.

I scooted lower on her body, so I could massage her ass.

"Doctor, I believe you are getting me wet," said Charlotte, breaking the silence in the room. "Your cock is dripping on me."

Indeed, it was. My arousal over Charlotte had me pre-cumming, since she first became naked. I did the reasonable thing. I rubbed my natural lubricant onto her ass.

"Let me sit between your legs," said I.

I lifted up to allow her underneath legs movement then sat down upon my knees.

Both my hands rubbed over her young firm cheeks. My hands frequently went to my cock to obtain more lubricant for her ass. A squeeze of her cheeks demonstrated the firmness that only youth provided. It was not long until her entire ass was sticky with my cum.

I trailed my index finger down her crack. She was incredibly still for an action that often was ticklish. It was an indication of her deep relaxed state. I probed my finger into her pussy. She opened her legs wider and allowed me better access.

When I pulled my finger out, it contained the mixture of juices of Bones and Charlotte. I ran the juices along her crack. I repeated the action again and again and often rubbed the juices on her anal hole. Her hole puckered on my first initial touches, but I took the necessary time so she became used to my touch.

I inserted my finger into her quim and swirled it around inside. I brought my finger to her hole again but I kept my finger extended and slowly pushed it inside of her.

"Doctor?" Charlotte said. Trepidation was in her voice.

"Feel my finger inside your ass, Charlotte," said I to soothe and calm her. "See how good if feels to you."

I pushed into her hole to my second knuckle. She breathed hard.

I slowly pushed my finger deeper into her hole. When my digit was fully inserted I left it there. Her ass muscles involuntarily clenched against my finger. I waited motionless for a long period until the tremors subsided. I did a slow circle inside her hole. Her ass tremors resumed but they subsided faster this time. I pulled my finger slightly out and then snuggled it fully back inside.

Charlotte exhaled breathily.

I repeated the finger retreat-and-return.

"Ahhhhhh," Charlotte moaned with heavy gasps.

In a few minutes, Charlotte pushed her ass back at my finger.

"How are you feeling?" I inquired as I slowly finger boffed this beautiful fourteen year old's ass.

"Wonderful," said Charlotte, "and a little strange. I feel surprisingly good."

Things had proceeded reasonably with Charlotte. Bones was not expected back in over an hour. I was increasingly hopeful that I would be able to confer to him that I was successful.

I slowly pulled my finger completely out of her hole. Her right hand came immediately to her hole and she slowly felt it.

"Get up on your hands and knees and we will continue."

She got up as per my request and looked back at me.

I grabbed my cock and lined it up with her pussy. I held her hips with both hands and thrusted into her.

Young Charlotte's head snapped up as she felt me enter her. She was plenty lubricated inside her quim, but I still required a firm push to get my fatness fully inside her. Her inner walls stretched as I pushed forward. I could not match the length of Bones, so I could not touch her depths like he could, however few men could match the snug fit that my cock provided inside a woman's pussy.