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My First Anal Experience

Posted Sunday, July 25th, 2010


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I’ll never forget the night I met Dara. Dara was a lot of firsts for me. My first older woman (I was 20, she was 27), my first black woman, and my first anal fucking experience.

My friends and I were out on a night on the town because I was headed off to Japan to teach English for a year. We headed out to this new bar that was getting a reputation for being a cougar bar. My friends dared me to see if I could get a genuine cougar but I’d already had my eyes on Dara the second we walked in the door. She was small and petite but with these amazing curves that made me think very dirty thoughts. Her ebony skin made her seem like only a shadow in the dimly lit bar but she had eyes that glowed with desired and lust - something I had never seen on a woman before.

I played it cool at first as I watched her on the dance floor with her friends. She really knew how to move and I was hoping that would carry on later in the night. The sway of her full hips had me hypnotized. I figured she had to come off the floor eventually so I stood near the beer girl and watched for her. When I saw her leave, I quickly paid for a cold one and headed towards her.

I caught her as she reached her table and put the beer in her hands. She eyed me up and down, grabbed my hand, and pulled me out onto the patio. The music was quieter so we began to talk and flirt.

It was only an hour later when we headed back to her downtown condo. Apparently she knew what she wanted and I was it. I had no clue that anal fucking was at the forefront of her mind.

The door was barely closed and we hadn’t even kissed yet before she was taking her clothes off. She pushed me against the wall and had my pants down around my ankles. She began to lick by balls and suck at my cock. I couldn’t believe how fast she got me hard and I’d never felt someone suck me off so well that it made me want to come within minutes.

She stopped just short though and without a word she led me to her room. She wasn’t a talker this woman - she was a do-er. She wasted no time pushing me to the bed, then straddling me. Her cunt was dripping wet and I watched my dick disappear in one swift movement, all the way to the balls, inside her. She rode me nice and slow at first. Then she got faster and faster. She was rubbing her clit like crazy and I thought she was going to cum, but suddenly she stopped.

She turned around so I could see that gorgeous ass and grabbed my dick. I thought she was going to slide it back into her pussy but she just rubbed it over her lips and then aimed it at her puckered little hole. First, just the head of my dick slipped in and I thought, “Holy shit - she’s going to fuck me with her ass!” And she did. Slowly but surely she pushed against my cock and took it all. I could believe that this hot ebony babe was into anal fucking!

It was fucking amazing. Her ass was tighter than anything I’d every felt. I had to concentrate hard on not cumming but I couldn’t help pumping her a little. She was pulling at her nipples and rubbing her clit again. She began riding my cock with her ass fast and she took it deep and I just couldn’t take it anymore. I knew that this anal fucking was NOT her first time! I came deep in her ass and she was right behind me with an orgasm that gripped my tool and sucked every last ounce of energy out of me.

She disappeared into the bathroom and I could hear her cleaning herself up. When she came out she kissed me on the cheek and thanked me. It was like anal fucking was second nature to her.

“Thanks hon. That was great. You fuck pretty good for a white boy. Do you need money for a cab?”

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