Anal Training Part 2 -The Entering

It had been over a week since Teacher and I last had any true action. Yours truly spent the last several days a pent up, cranky, frustrated mess. Honestly, I can't not even begin to tell you all how much I needed a release. My own hands, nor electronic or battery operated implements could do the job. Why? It was, apparently not just an orgasm that my body and psyche craved, but my new drug of choice-physical pain. Lord knows I had oodles of psychological pain-it was this big empty hole in my chest that needed to be filled. I tried to fill it one night with Jagermeister and beer. Of course (duh!) that only left me with a hangover and an embarrassing call to Teacher to drive my hungover ass to my car. I just wanted to get it all out and I didn't know what to do, I contemplated cutting--something I've never done, and ultimately decided was not for me. I just held on.


Last night Teacher and I had a lovely evening. He picked me up looking all sorts of hip in a Johnny Cashesque black shirt and black tie which contrasts perfectly with his long blondish hair and baby blue eyes. Once in his car, I felt myself go back to my normal bubbly demeanor. After a lovely dinner we went back to my little lair in the ghetto.

We were barely in the door when he got a fist full of my hair and kissed me deeply. In seconds flat we were in my bedroom with our clothes off pawing at one another.I found myself chewing on his lip, gnawing and scratching at his body and he chewing on my neck and nipples. I say there nothing more delicious in life than being in that primal state acting like feral beasts.

It was pretty obvious at that point that we were not going to be getting into a heavy BDSM thing. If Teacher were writing this, I think he'd tell you that little ol' me can be quite the temptress if I may brag a little.(I was told later that he had planned all night to tie me up, but the need for my pussy overruled that desire)Teacher did take the time to spank my needy ass.

Bare palmed he whacked my butt which apparently had gone back to it's virgin tenderness. He started out with mild spanks that slowly build up to major cheek punishment. Each time his hand met my bottom I found myself chewing on my bedspread to stifle my cries.

After Teacher laid his hand on me for the last time, I was flipped over, legs forced apart. He dove into my my cunt like it was the first one he had ever seen. As he lapped at my clit, and chewed on my labia I started thinking that perhaps maybe a finger up the old ass would be a good add-on. I tapped his head, and you'd think a foul-mouth chick like me would have no qualms asking for some anal play, but I got all hot faced and mumbled my wish. There was no argument.

Teacher reached for the lube, and he finger fucked my tender baby of an asshole as he continued to tongue my pussy. Unlike the time before, I felt much more relaxed, I actually started to really, really dig it. In my mind there were more than one finger inserted, so I figured OK I can handle the cock.

I sat up, alarming Teacher, I gasped, "OK, I'm ready for it, I'm ready for your cock in my ass."

"Put your hands on the bed," he said. I did as told. I was standing up, with my ass towards him, face towards the headboard. I heard the bottle of lube click open. "Oh crap," I thought, "what am I thinking?" But I figured it was now or never, I was ready as I'd ever be.

Teacher moistened both my backhole and his dick with the lube. "I'm going to take it easy on you X."
Immediately I started breathing very heavily. I was shaking. Goosebumps broke out on my arms. I stretched a bit forward. He held on to my shoulder and I felt the head of his cock enter. I panted, "Ok, ok..more."
It seemed like forever, but as he slowly entered me, I felt myself release my body to accept him into me. For lack of a better way of describing it, it stung a little as my rectum was stretched out, but I also simultaneously felt the pressure like I had never felt in my pussy before, and I could feel the pressure of his cock in my pussy via my ass. It was intense. He paused, "Are you OK, X"
"Uh-huh," huff, puff.."Go on."
He didn't stroke to hard, he was kind that way. It felt good, painfully good as his cock slid in and out, but it got to the point where still I couldn't continue. I still apparently could not handle the full intensity of a big cock in my ass. I didn't want to disappoint him, but I didn't want to be a big shot. We paused again.
"I think I need to stop Teacher" He obliged, and then pulled me into his arms and hugged me. Then it happened.
I started shaking.
I started crying a little.
"Are you OK X?"
"Yep" I said as he wiped the tears from my eyes.
He hugged me again and then I just lost it, I was a sobbing little mess. Can I just tell you guys It was just an insaneo moment where I was a tad overwhelmed with some memories, a tad happy,a tad turned on, and well my mind was fucking blown.I just had to let it all out. Teacher soothed me and I realized he, unlike any man I have ever known my life does not flip out when I cry. Last night while it was not assorgasmic, I felt closer to him than ever.

After the tears had dried up and we had relaxed, I walked to the corner of my room and retrieved his rattan cane. "Can you?" I pouted a little. Hell, I just caught myself pouting as I wrote that! "But of course," he said. I got on all fours on my bed. He started thwacking it on my ass. I was like "this doesn't feel like shit!" I resumed to a "la di da" yawn position, when the caning picked up speed. Oh hell did I learn my lesson that! Wack!Wack!Wack! I also learned that putting my butt down instead of up is pretty fucking stupid. Boy did it hurt and boy did it feel great! Finally though, I couldn't even mutter my safe word, I just writhed over to the corner of my bed and put out my hand.."pleasssse..stop..enough." He did. As I turned back to rub the stripes on my tush, he entered me from behind.

So dear readers, while I'm still en route to being an anal slut, I'm not minding the journey at all.

Ramble on....


Kinky Aoefe said...

Great job in the telling! I love anal - it gets better and better - just sayin. :)


His pet said...

That was great! i just wrote about anal play (not nearly this beautifully though). i am glad that your Teacher is gentle and patient with you. AND he can handle tears? You better hold on tight to him!! My Master tells me to suck it up or 'pull it together for me pet'. i love that your Teacher held you while you cried all the feelings out. Good for him (and you).


irishsub said...

So glad I found your blog, I'm trying to stump up the courage to try anal again after an awful experience with an incompetant. Sometimes I get so frustrated that it seems to easy for others, relief to read your tale...

Severine said...

Tell ya what, after you do it for a while, and as long as you use lube, it will feel as easy-going as vaginal sex - at least that is my experience. But then if you don't practice, it's harder again, I found.

A Nawty Mouz said...


Wow, intense. He touched a depth in you (fondo comes to mind), like a deep in the ocean. And, he held you and didn't let you fall. Teacher is a good teacher. He has control of himself and a handle on what is happening.