Feminist Pornographer

A few weeks ago, I posted about teachmyass.com, a porn site with a fantasy concept I find totally hot and totally absurd. Anal virgins – innocence lost to hardcore sex acts – hot. Anal virgins eager to learn – so eager they pay some anal expert dude to teach them how to take fingers, toys and his cock in their asses – hot and absurd. Here’s “Allie” submitting her application and paying for the privilege of having her ass prodded and poked:

Just to make sure you’ve caught Allie’s back story, here’s the text in her collage:

Allie 18 years old
Allie came into my office with a sweet little puckered virgin asshole! I dragged out some of my favorite sex toys including a butt plug, a long rubber dildo, and my best anal beads to get her nice and loosened up! Then when I finally stuffed my dick in her ass, she was nice and tight engulfed around me! I nailed her for quite awhile and then left her virgin ass gaping wide!

Teach My Ass was at the center of one of my peak sexual experiences with D – my first pleasurable anal experience, in fact. I wrote about that experience in my last teach-my-ass-based post. The relevant details I’ll reiterate here are…

D planted me in front of the computer, naked from the waist down. He brought up the site’s opening galleries – for example, Deniese’s gallery:

Did you catch Deniese’s back story? Here it is:

Deniese 20 years old
This lovely lady came into my office just begging me to fuck her in the ass! Slow down, Deniese, we have to give your little rear end a good stretching first! So I lubed her up good and plenty and slid in a long butt plug – she seemed to really like that! However she REALLY liked it when I stuck two fingers in her ass and two fingers in her pussy! She loved getting double penetrated!

So D brought up this porn site with these sweet college-aged girls begging to be anally penetrated. Then, with D looking at my own sweet ass from the same vantage point that the camera looks at the models’ asses, I was inspired and ready for him to teach my ass new tricks. That day I learned to enjoy 4 fingers double-fucking me – two of D’s fingers in my pussy and two of D’s fingers in my ass.

The finger-fucking was good, but we agreed that during my next visit, we wanted to try out full-on cock-in-ass fucking – it would have been a first for both of us. Alas, D never fucked my ass with his cock. We tried to get there, but our relationship was fraught with problems, and I remained an anal virgin after the last weekend we spent together. For two years after ending things with D, I periodically longed for him, his anal skills and another attempt at our plan to lose our anal virginities together.

And sometimes ….

I fantasized about attempting to woo him back into my bed/ass, by emailing him my own Teach-My-Ass-type back story. For my teachmyass.com parody, I had something like this in mind:

Marilyn 32 years old
Sweet and shy Marilyn was desperate to have her ass stretched! Still an anal virgin at the embarrassingly old age of 32, she was ripe and ready when I stuffed a glass dildo in her and poked around inside with my thumb! That loosened her tight little asshole up to take my dick nice and deep! Marilyn couldn’t get enough anal penetration!

I’m glad that emailing the above to D remained a fantasy and that my ass didn’t take a cock to its base until I met C, wonderful C. C is the anal expert teaching my ass in my official Teach My Ass homage: