Asses etc.

Simon, my then boyfriend, had wanted to do me in the ass for long time. It was an act that I had resisted for a long time after a bad experience some time previous. It was, and remains, one of the few sexual acts that I have conflict with.

Simon did his best to comfort me, and eventually I consented to the act, but on one condition: What he got to do to me, I got to do to him. And that I got to go first.

We planned for this to happen one weekend in August, when he and I, and a bunch of other people we knew were driving down to Washington DC for the weekend for a TNG (a leather group for younger people in the scene) event at a leather club down there, hosted by their own TNG group.

We drove down in a car with two other people, among them my friend Cora, along the way she and I flashed truck drivers, pressing our breasts up against the cool glass and getting them to blow their horns.

The hours leading up to our plan were fairly tame, Cora and I did a fight scene which didn't really go anywhere, and eventually Simon and I found our way back to another. "I want to fist you," he said bluntly. I nodded consent and followed him passively upstairs to a quiet corner where I laid back in a sling, and put my feet up on the chains.

He slowly began pressing fingers into me, gently but firmly rocking his hand against my cunt. He got four fingers in, and when he went to press his thumb into my cervix, I gasped in pain and screwed my eyes shut. He pulled back, and took his time. His thumb found it's way to my clit, and he began rubbing his fingers against me. I jolted with the pleasure and pressed myself down against him.

"I'm going to come," I gasped, and then I threw my head back, and I screamed, loud and long. I could hear my voice echoing throughout the warehouse as I pressed and arched and rode out the waves until I laid in the sling, stupid with pleasure.

Simon withdrew his hand and rolled on a condom, and pressed down into me, seeking his own pleasure which came a few minutes later. He pulled out and pulled off the condom and came on my belly. After a while we cleaned up and sheepishly walked towards the stairs. When we entered the main room, Cora, in her infinite energy burst into applause and I smiled ruefully. 

We ate dinner and it became closer to Simon's moment. Another friend of ours loaned us her strap-on (similar to the one I would buy later on, after Simon and I parted ways), and she settled me into the harness, and Simon and I found a comfortable spot. I rolled a latex glove onto my right hand, since I didn't want to hurt him with my fingernails.

I began rocking into his ass the same way he had tried to work his way into my pussy several hours earlier, finally when he was ready, I pressed down into his ass and began rocking back and forth. I gasped, my thighs warmed and heat flooded my face. It was amaaaazing! I had never felt anything like it, and I pressed down into his ass, as intent on my own pleasure as I was on his. I can only imagine how much better it is with a bio-cock. I did not want this to stop, and I moaned as I sawed into him. I was vaguely aware of people murmuring about this, and I would later be approached to be told how hot it was to watch what we were doing. I was lost in the sensations, the both of us moaning. Simon's head hung down against his chest, and my head was thrown back, lips parted and eyes closed.

After a long while, Simon called it quits, and I pulled out of his ass. Neither of us came, but doing this had left me feeling fortified; I no longer had to be on the receiving end when it came to cock. Now I had choices.