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My ass soaked in numbing cream, my sissy clit dripping from the chastity, and my body feeling orgasmic in every touch and sense. I have never been to a sex shop before so I wanted to be prepared, I dressed up under normal street clothes and made sure there wasn’t a hair on my body. My nails painted and my panties on I know were the only things I will be wearing when on my knees sucking cock after cock. But I dressed up in a one piece lingerie with a few other essential things like jewelry and stockings and high heels in my carry bag if the man I was sucking off demanded I wear something like that.It was late, 10 at night, and the shop was closing in a few hours so I hurried up and gathered my things and drove to the lot. My heart racing and my cock was aching to be released from its device. There was no going back now, after pulling in the parking lot the amount of cars there was making me really nervous. I could hardly find a parking spot! I wondered why there was so many cars here. I turned around and spoke into his ear. “I want you to fuck my ass.”He said something back that I couldn’t hear over the music, but it wasn’t hard to tell that his response was positive. Twenty minutes later we were back in his bedroom. He took me from behind and gave me what I was craving. His thick cock filled me, stretching my asshole and sending pleasure through my whole body.The night I lost my anal virginity, I said the same exact line. “I want you to fuck my ass.” Of course, the situation was very different and it wasn’t planned by any means.I lied to my parents to sneak out of the house. They thought I was going to sleep at my best friend’s house. Instead, I drove to my then boyfriend’s apartment.We didn’t usually have a lot of time together in private. Usually, quickies in the car after work in a near empty mall parking lot (we both worked at the same store) or quickies at his apartment before I had to race home. This time was different, we had all of the time in the world.
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