The first thing I ever saw of E was his toned, pale ass.  As instructed, he was on all fours facing the window and my favorite champagne was chilling on the table.  Isobel (a kinky acquaintance) and I changed from street clothes to gloves and corsetry, et cetera before sitting down to observe our slave-for-the-evening.  Neither of us had met him before but he came with trusted references and an impressive openness to experimentation.  Fresh out of a bad marriage, he could have bought a motor cycle or grown his hair long but instead put his hand up for an ass-fucking by two unknowns.  We didn’t let on but we were impressed–he’d followed our instructions exactly.  He’d gotten a hotel room at the requested establishment, acquired a specific vintage of Laurent Perrier and Marcolini chocolate, and was ready and waiting when we arrived.  He’d told us that this was going to be his first experience as a submissive and requested that we be gentle, especially with any strap-on activity.

One of the purposes of the evening was for me to try out a strap-on.  Isobel had done it many times and when we came up with the idea of playing together, I said I wanted to learn. It was a personal play date and a chance to do whatever I wanted.  Still, I’m always cautious about other people’s boundaries/limits, while Isobel couldn’t care less.  She openly admitted that if someone doesn’t please her or do what she likes, she just gets rid of them.  Her approach to domination is more like annihilation–if you’re a slave you have no boundaries or limits, that’s why you’re a slave. Philosophically, she has a point and the truth is that our prior communications with E didn’t delude him into thinking that we’d be gentle or considerate.  Still, I feared for E’s ass on his behalf and decided to be a little bit of a buffer by fucking him first.  It was interesting, not really erotic but clearly a powerful act.  I didn’t push it too far and E seemed ok, although he wanted a cigarette pretty desperately afterward.  Then I sat back with a drink to watch the other two.  Isobel’s strap on was quite a bit larger than mine. She took a hold of the collar around E’s neck before inching in from behind, while he gasped for air out of nervousness.  It wasn’t funny but it was.  A few minutes later he let out a really loud scream and I could tell that it wasn’t from pleasure.  There was some commotion and he ran to the bathroom in a panic.  Although anal play can hurt if not done carefully, it’s rarely physically dangerous.  I told him he’d be ok and he said he was fine but that he didn’t think ass fucking was for him.  Glad he tried it though.