I think one of the naughtiest things I have done happened about two years ago. I was recently divorced and just out of my mind. I hadn't had sex in months and when a college age guy started flirting with me, I flirted back. Hard. In retrospect, I may have taken things just a little further over the top than I should have, but here's basically what happened:

We met at a coffee shop, had a few drinks, I invited him back to my apartment for something stronger... some twenty minutes later, I had him down to his shorts and I was wandering around my house in my bra and panties, austensibly looking for something I wanted to try on to get his opinion... we made out some...  I told him he should go upstairs to my bedroom and use the handcuffs in my drawer to cuff his hands over his head to my headboard.  I stayed downstairs and waited a few minutes.

Entering my room, there he was, grinning, a tent in his shorts! (which i slipped off of him almost immediately) I used a couple pairs of leggins to tie his legs to either side of my bed's foot board... legs open a bit like a V. He was kind of giddy, kind of pretend-strugglin. He had no idea what he had coming to him.

I stuck a viagra pill up his asshole. Which works just like swallowing it, except it can be DONE to you.  I went back downstairs to fix a drink. I came back up, drink in hand and let my bra fall to the floor. He was there, breathing harder

 "Oh my-god.. what did you DO to me?!!!" 

"Whats the most times you've fucked in a single night? Be honest"

 He said it was probably four or five times. His erection was noticably tighter. His nuts were pulled up tight. I knelt on the bed between his legs, he made an actual struggle to try and sit up.. to touch me... to anything... chains of cuffs wrattling on the iron headboard. He was 21. And so I simply leaned forward to begin the process... he could in no way prevent my tongue from licking up the inseams of his legs. My tongue from licking under his balls. Its tip tracing up one side of his shaft, around the purple swollen head, and down the other side. I sucked one nut into my mouth.

And for the next eight hours, we were each other's oblivion.

He came eleven times. I came eight. Sometimes he still calls me when he breaks up with a girlfriend or it is late at night and he is awake by himself with desparate pangs of lust and his memories...