My wife becomes my Mistress a long time ago but I still remember the first time she ever started to play with my ass. We were in some heavy lovemaking and she was sucking my cock and pulling on my balls all of a sudden she started playing with my ass. First taking her finger and tapping my asshole then she rubbed the outer edge of my ass.
I noticed my cock was jumping all around and pre-cum was forming on the end of my cock, I told her that it felt real good and she said let me finger your ass. Well that was the start of a new sex life before the night was over she had fucked me with 3 fingers, my ass loved it and I was too. Over the next 4 weeks she had fucked me with a thin carrot with a condom on it and I was able to relax a lot now when ever I was ready to cum she would play with my prostate and I would cum more than ever. I started playing with my ass whenever I was alone masturbating I never let her know that I was starting to fuck myself with cucumbers, Hair brushes and thick candles.
Until one day she come home early and sneaked into the house I was laying in the bedroom masturbating with a big cucumber stuck all the way up my ass when I saw her It scared me and my ass tighten up and I shot that cucumber have way across the room. I thought she would be mad but she was amazed I could take something that big in my ass. She walked over to her dresser drawer and pulled out a vibrating dildo and said that I was a bad boy and that if I didn't let her fuck me with the dildo she would cut me off of sex for a month.