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My first anal experience was a few months ago when at 51. I was dating a 29-year-old man. My lover had guided me back from a dry period following the break up of a long marriage. It was an incredible turn on for me to have this young virile guy so attracted to an older woman. I had never had anal sex but was curious. He was experienced and willing to be very patient. I worried about the "mess." He assured me it would be fine.

We started with anal play and touching during our lovemaking sessions. He applied gentle pressure and circling motions. One night when I decided I was ready for more, we started with vaginal fucking, doggie style. He did the usual anal stimulation, then applied lube to a butt plug. He gently and slowly inserted the plug into my ass, advancing it slowly as I relaxed. After I became accustomed to the feeling of his gentle thrusting, he asked me if I wanted him to put his cock in my ass. I was more than ready for that!

He removed the butt plug and showed me that it indeed was clean. He lubed his cock and slowly inserted just the head at first. At the same time he inserted a small vibrator into my pussy and positioned one hand where he could finger my clit. He moved slowly until his cock was completely inside me, then pulled back and began to gently thrust. I was surprised to hear moans from myself in a pitch I have never before uttered -- deep throaty sounds. It was the most incredible feeling I have ever experienced with sex.

He continued to ask if I was alright and whispered sex talk in my ear while thrusting. It was difficult for me to talk but between gasping breaths I got the message across that I wanted him to fuck me hard. I pushed back into him and he used his free hand to hold my hip as he pulled me to him. I came before he did but continued to enjoy the experience as he spoke into my ear describing what it felt like to him...eventually asking me if I wanted him to come inside me before he filled my ass with his sperm. I can still remember how it felt as he tensed and shot his load deep inside me.
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