If at First You Don't Succeed...

The last time I had sex with the Boss was the first time I attempted anal with him.  I use the term "attempted" because like most of my sexual escapades, it was doomed from the start.  I had yet to be convinced that I would enjoy that particular sexual act so it was strictly forbidden.  However, I had been more and more receptive to the idea in the months leading up to this encounter.  The Boss and I discussed it and he was trying to hide his excitement as he played it off like it was no big deal.  Imagine my shock when I arrived at his apartment to find...nothing.  Well, very little.  He shrugged off my questions and said  he was giving his furniture to his son but I knew he was lying.  You don't give your son the pictures off your wall and even if you do give him your bed, you don't give him your sheets and blankets, too.  My mind was racing.  Why lie to me?  Why not admit he was moving?  Then it hit me...he was moving in with a woman.  Rather than tell me the truth and risk my rejection, he lied to me so I would have sex with him one last time.

I should have left him there with his hard-on and empty walls.  I wish I could say I told him to fuck off and that was the end of us, but you already know that isn't true.  I let him lead me upstairs to his empty room and lay me down on the outstretched blanket on his floor.  If I had not let him kiss me, I may have just left but if you read my last post you are aware that we have this crazy physical attraction.  Once he kisses me, it is over.  The next thing I knew I was on all fours and he was behind me trying his best to slowly but boldly go where no man had gone before.  My mind was racing still.  I couldn't stop thinking about the lie.  He knows I know he fucks other women.  I have only mentioned it once and that was only to ask if he uses protection with them every time.  He knows I am not jealous or spiteful.  Why lie TO ME? 

I could not relax.  Gentlemen, in case you don't know, anal sex is quite impossible, especially if it is her first time, if she is not relaxed. Even if you forge ahead, it will NOT be enjoyable.  He barely touched me with the tip when I made him stop.  The disappointment on his face was obvious.  He managed to pull himself together and fuck me anyway despite his great loss (yes, that's sarcasm).  He rushed me out the door and I felt so sick to my stomach.  I knew it was coming and then...

The phone chirped.  He sent me a text letting me know that we had just had our last fuck.  I knew in my heart he would be back (I was right) but I took the opportunity to vent (just a little) and let him know that I didn't appreciate being lied to and he should never contact me again.  I meant it at the time.  I just knew he would contact me again and boy was I going to tell him a few things...

Six months later I get a message from him.  He wants to chat (fuck me) and wants to know if I am mad.  I should have ignored him.  I answered back that I was hurt not mad and we began to flirt and banter like nothing happened.  In fact, although he has confirmed he is living with someone new, we have never discussed it.  I feel it is none of my business.

I did get a little satisfaction in telling him that since our last encounter, I have not only had anal sex, I enjoy it.   He has told me that it is unfair that someone else was first and he has thought about my ass every day since that attempt in his apartment.  I have enjoyed teasing him.  I have been teasing him now for a couple of months but I am a girl who likes to fuck so...